Co-reporter:Xiaobo Huang, Bingchuan Zhang, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2017 Volume 27, Issue 18(Issue 18) pp:
Publication Date(Web):15 September 2017
DOI:10.1016/j.bmcl.2017.08.031
To develop natural-product-based pesticidal agents, a series of monosaccharide-related ester derivatives (17a–q and 18a–f), glucose (xylose)-piperic acid/piperic acid-like conjugates, were synthesized. Three-dimensional structures of compounds 17b, 17g, 17h, and 17n were unambiguously determined by single-crystal X-ray diffraction. Especially compounds 18e and 18f exhibited the most potent insecticidal and acaricidal activities against Mythimna separata and Tetranychus cinnabarinus. Their structure-activity relationships were also discussed.Download high-res image (116KB)Download full-size image
Co-reporter:Yong Guo;Ruige Yang
RSC Advances (2011-Present) 2017 vol. 7(Issue 45) pp:28009-28015
Publication Date(Web):2017/05/25
DOI:10.1039/C7RA03588H
In continuation of our program to discover new natural-product-based crop protection agents, we prepared a series of esters and oxime esters/sulfonates from furyl-ring-based acetylation derivatives as pesticidal agents by structural modification of fraxinellone, a biorenewable degraded limonoid isolated from Meliaceae and Rutaceae plants. The structural assignment was based on the spectroscopic and X-ray analysis data. Their insecticidal activity was evaluated against a crop-threatening agricultural insect pest, Mythimna separata Walker. Among all derivatives, compounds 9a and 10i exhibited the most promising pesticidal activity. Their structure–activity relationships were also discussed.
Co-reporter:Jiu-Lin Huang;Min Lv
RSC Advances (2011-Present) 2017 vol. 7(Issue 26) pp:15997-16004
Publication Date(Web):2017/03/09
DOI:10.1039/C7RA00954B
In continuation of our program to discover new potential natural-product-based crop protection agents, we synthesized a series of 14-formyl-15-aryloxy/methoxymatrine and 14-aryloxymethylidenylmatrine derivatives as pesticidal agents by structural modification of matrine, a biorenewable quinolizidine alkaloid isolated from Sophora flavescens. The structural assignment was based on spectroscopic and X-ray analysis data. Their pesticidal activities were carried out against two typically crop-threatening agricultural insect pests, Mythimna separata Walker and Plutella xylostella Linnaeus. Compounds 4i and 4k exhibited more potent oral toxicity than matrine against 3rd-instar larvae of P. xylostella. As compared with matrine, all derivatives displayed a growth inhibitory property against early 3rd-instar larvae of M. separata, and in particular compounds 4i–k displayed more promising insecticidal activity than toosendanin. Some interesting results of structure–activity relationships were also observed.
Co-reporter:Yuanyuan Zhang
RSC Advances (2011-Present) 2017 vol. 7(Issue 56) pp:35191-35220
Publication Date(Web):2017/07/11
DOI:10.1039/C7RA04715K
This review covers the isolation and structure determination of limonoids reported during 2014–2016 (with 363 new compounds in 68 papers), together with the relevant biological activities and source organisms. Furthermore, the total synthesis and structural modifications of limonoids and their analogs regarding the bioactivities reported during 2011–2016 have also been summarised.
Co-reporter:Ruige Yang, Xiaobo Huang, Zhiping Che, Yuanyuan Zhang, Hui Xu
Industrial Crops and Products 2017 Volume 107(Volume 107) pp:
Publication Date(Web):15 November 2017
DOI:10.1016/j.indcrop.2017.05.033
•A series of 2'-chloro/bromo-5-bromopicropodophyllotoxins were prepared by structural modification of podophyllotoxin as pesticides.•Compounds 6a and 7a exhibited more promising insecticidal and acaricidal activities against M. separata and T. cinnabarinus.•The interesting structure-activity relationship was observed.Podophyllotoxin is isolated as a sustainable natural bioresource from the roots and rhizomes of Podophyllum hexandrum and Juniperus Sabina. In continuation of our program aimed at the discovery of biorenewable natural product-based pesticides, a series of 4α-acyloxy derivatives of 2'-chloro-5-bromopicropodophyllotoxin or 2',5-dibromopicropodophyllotoxin were synthesized by structural modification of podophyllotoxin, and evaluated as insecticidal and acaricidal agents against two serious agricultural pests, Mythimna separata Walker and Tetranychus cinnabarinus Boisduval. Among all derivatives, compounds 6a and 7a exhibited more promising insecticidal and acaricidal activities than podophyllotoxin, and the final mortality rates of 6a, 7a and 1 against M. separata (at 1 mg/mL) and T. cinnabarinus (at 0.5 mg/mL) were 50%/53.3%/36.7%, and 33%/41.8%/1.6%, respectively. This suggested that introduction of the acetoxy moiety at the C-4 position of 2'-chloro-5-bromopicropodophyllotoxin/2',5-dibromopicropodophyllotoxin was necessary for the insecticidal and acaricidal activities.Download high-res image (188KB)Download full-size image
Co-reporter:Xiang Yu, Gang Feng, Jiulin Huang and Hui Xu
RSC Advances 2016 vol. 6(Issue 36) pp:30405-30411
Publication Date(Web):14 Mar 2016
DOI:10.1039/C6RA00993J
In continuation of our program aimed at the discovery and development of efficient insecticidal agents, a series of quinoline-based hydrazone derivatives were synthesized and evaluated as insecticidal agents against three-day-old larvae of Spodoptera litura (Noctuidae: Lepidoptera), a polyphagous insect pest of many important crops, in vivo at 1 mg mL−1. In particular, compounds 3c, 3e, 4g, 4h, and 6f showed potent insecticidal activity with 7 day mortality rates greater than 93%, and were comparable to that of the positive control toosendanin.
Co-reporter:Qin Li, Xiaobo Huang, Shaochen Li, Jingchun Ma, Min Lv, and Hui Xu
Journal of Agricultural and Food Chemistry 2016 Volume 64(Issue 27) pp:5472-5478
Publication Date(Web):June 24, 2016
DOI:10.1021/acs.jafc.6b01995
A total of 20 esters of fraxinellone C4/10-oxime were synthesized and determined by melting points, optical rotation, infrared spectra, proton nuclear magnetic resonance spectra, and high-resolution mass spectrometry spectra. Two steric configurations of compounds 7i and 8i were unambiguously confirmed by X-ray crystallography. Additionally, their pesticidal activities were assessed on two typical lepidopteran pests, Mythimna separata Walker and Plutella xylostella Linnaeus. Generally, all compounds exhibited less potent oral toxicity than toosendanin against third-instar larvae of P. xylostella. However, all compounds showed the growth inhibitory property against early third-instar larvae of M. separata. Notably, compounds 7m, 8b, 8k, 9, and 11 displayed more potent pesticidal activity than toosendanin. This demonstrated that introducing the C-4 carbonyl or oxime group on fraxinellone resulted in more promising derivatives than those bearing a C-10 carbonyl or oxime substituent.
Co-reporter:Rong Wang, Xiaoyan Zhi, Jie Li, and Hui Xu
Journal of Agricultural and Food Chemistry 2015 Volume 63(Issue 30) pp:6668-6674
Publication Date(Web):July 12, 2015
DOI:10.1021/acs.jafc.5b02036
To discover novel natural-product-based pesticidal agents, we prepared a series of oxime sulfonate derivatives of 2′(2′,6′)-(Di)chloropicropodophyllotoxins by structural modification of podophyllotoxin. Their structures were well-characterized by proton nuclear magnetic resonance (1H NMR), high-resolution mass spectrometry (HRMS), optical rotation, and melting point. Moreover, the key steric structure of compound 5f was unambiguously determined by single-crystal X-ray diffraction. Additionally, their insecticidal activity was evaluated at 1 mg/mL against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker), a typical lepidopteran pest. Among all derivatives, compounds 4c, 5c, and 5d exhibited more promising insecticidal activity, with the final mortality rates greater than 60%, when compared to their precursor podophyllotoxin and the positive control, toosendanin. It demonstrated that introduction of the chlorine atom at the C-2′ or C-2′,6′ position on the E ring of picropodophyllotoxin or oxime sulfonate derivatives of picropodophyllotoxin was important for the insecticidal activity and introduction of a halogen (e.g., fluorine, chlorine, or bromine) atom-substituted phenylsulfonyl group on the oxime fragment of 2′(2′,6′)-(di)chloropicropodophyllones could lead to more promising compounds.
Co-reporter:Xiang Yu, Danfeng Shi, Xiaoyan Zhi, Qin Li, Xiaojun Yao and Hui Xu
RSC Advances 2015 vol. 5(Issue 40) pp:31700-31707
Publication Date(Web):27 Mar 2015
DOI:10.1039/C5RA01411E
As part of our ongoing search for new insecticidal agents originating from natural products, in the present paper, we have prepared a series of C7-oxime ester derivatives of obacunone and evaluated their insecticidal activity at 1 mg mL−1 against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker), a typical lepidopteran pest. The structures of all target compounds were well characterized by 1H NMR, HRMS, optical rotation, IR, and mp. More importantly, three key steric structures 3m, 3r, and 3s were unambiguously determined by single-crystal X-ray diffraction. Compounds 3e, 3r, 3s and 3w exhibited more promising insecticidal activity with final mortality rates greater than 60%, when compared with their precursor obacunone and toosendanin (a positive control). For the C7-oxime alkylester series, the appropriate length of the side chain at the C-7 position of C7-oximeobacunone was very important for insecticidal activity; for the C7-oxime arylester series, introduction of the chlorine atom on the phenyl ring at the C-7 position of C7-oximeobacunone could lead to the most potent compounds. According to the QSAR model, five descriptors such as RDF100v, RDF105u, Dm, Mor15m and R1u, were likely to affect the biological activity of these compounds. Among them, the most important one was RDF100v. The correlation coefficient (R2), the cross-validation correlation coefficient (Q2) and the standard deviation error in prediction (SDEP) are 0.891, 0.835 and 0.0358, respectively.
Co-reporter:Chun Yang, Xiaoyan Zhi, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 10) pp:2217-2219
Publication Date(Web):15 May 2015
DOI:10.1016/j.bmcl.2015.03.052
A series of novel benzoxazole compounds derived from a naturally occurring neolignan honokiol were prepared. Their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker) in vivo. Most of the tested derivatives exhibited more potential insecticidal activity than their precursor honokiol at the concentration of 1 mg/mL. Especially compound 6e, containing 4-acetyloxyphenyl groups at the C8 and C8′ positions, displayed the most potent insecticidal activity with the final mortality rate of 62.1%.
Co-reporter:Xiang Yu, Guodong Ding, Xiaoyan Zhi, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 1) pp:25-29
Publication Date(Web):1 January 2015
DOI:10.1016/j.bmcl.2014.11.027
Here we have prepared a series of ester compounds of obacunone, a naturally occurring limonoid, isolated from plants such as Citrus and Dictamnus angustifolius. Their insecticidal activity was evaluated at 1 mg/mL against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker), a typical lepidopteran pest. When obacunone reacted with NaBH4, the ratio of two reduction products, C7α-hydroxyobacunone (2) and C7β-hydroxyobacunone (3), was related to the reaction mixing solvents. C7α-Propionyloxybacunone (4b) and C7β-(n)heptanoyloxybacunone (5g) exhibited the more promising insecticidal activity than their precursor obacunone and toosendanin.
Co-reporter:Miaofeng Ma, Jili Feng, Ruoxin Li, Shu-Wei Chen, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 14) pp:2773-2777
Publication Date(Web):15 July 2015
DOI:10.1016/j.bmcl.2015.05.013
This study synthesized 20 sclareol derivatives. The antifungal activities of these derivatives were evaluated in vitro against five phytopathogenic fungi using the mycelium growth rate method. Among all the tested compounds, compound 16 with one iodine atom and three hydroxyl groups displayed higher fungicidal activities against all the tested phytopathogenic fungi than precursor sclareol. Compound 16 also showed more pronounced antifungal activities against Curvularia lunata (IC50 = 12.09 μg/mL) and Alternaria brassicae (IC50 = 14.47 μg/mL) than the positive control, a commercial agricultural fungicide thiabendazole.
Co-reporter:Zhinan Gao, Min Lv, Qin Li, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2015 25(22) pp: 5092-5096
Publication Date(Web):
DOI:10.1016/j.bmcl.2015.10.017
Co-reporter:Lingling Fan, Yong Guo, Xiaoyan Zhi, Xiang Yu, and Hui Xu
Journal of Agricultural and Food Chemistry 2014 Volume 62(Issue 17) pp:3726-3733
Publication Date(Web):April 14, 2014
DOI:10.1021/jf405316w
As part of ongoing efforts to discover new natural-product-based insecticidal agents, in the present study, an efficient method for the stereoselective α-chlorination at the C-2 position of 2′(2′,6′)-(di)halogenopodophyllotoxin derivatives was first developed. Subsequently, a series of novel esters of 2α-chloro-2′(2′,6′)-(di)halogenopicropodophyllotoxin with modified C, D, and E rings of podophyllotoxin were smoothly obtained. Finally, all of the title compounds were tested against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker) at 1 mg/mL. It was found that besides their 2′-halogen-substituted E ring, the stereoselective α-chlorination at the C-2 position of 2′(2′,6′)-(di)halogenopodophyllotoxins was also related to the chlorination reagents. Especially 2α-chloro-4α-(benzoyl)oxy-2′-chloropicropodophyllotoxin (6e) and 2α-chloro-4α-(2-chlorophenylacyl)oxy-2′-bromopicropodophyllotoxin (8f) showed the most potent insecticidal activities, with final mortality rates of >60%. For 4α-(alkylacyl)oxy derivatives of 2α-chloro-2′(2′,6′)-(di)halogenopicropodophyllotoxin, the effect of the length of their side chain at the C-4 position of podophyllotoxin skeleton on the insecticidal activity was not very obvious. For 4α-(arylacyl)oxy derivatives of 2α-chloro-2′-chloro/bromopicropodophyllotoxin, an electronic effect of the substituents on their phenyl ring at the C-4 position of podophyllotoxin skeleton on the insecticidal activity was observed.
Co-reporter:Juanjuan Wang, Xiang Yu, Xiaoyan Zhi, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 18) pp:4542-4545
Publication Date(Web):15 September 2014
DOI:10.1016/j.bmcl.2014.07.076
In continuation of our program aimed at the discovery of new natural-product-based insecticidal agents, twenty-six deoxypodophyllotoxin derivatives modified in the D-ring were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. The configuration of three compounds 3, 4, and IIIi was unambiguously determined by single-crystal X-ray diffraction. It demonstrated that aminolysis of deoxypodophyllotoxin in the presence of pyrrolidine and piperidine could result in complete inversion of the configuration of the carbonyl group at its C-2 position. Five compounds IIa, IIi–k, and IIIh showed the equal or higher insecticidal activity than toosendanin. Especially IIj displayed the most potent insecticidal activity with the final mortality rate of 65.5%.
Co-reporter:Xiaoyan Zhi, Xiang Yu, Chun Yang, Guodong Ding, Hui Chen, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 3) pp:765-772
Publication Date(Web):1 February 2014
DOI:10.1016/j.bmcl.2013.12.105
Co-reporter:Yi Wang, Xiang Yu, Xiaoyan Zhi, Xiao Xiao, Chun Yang, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 12) pp:2621-2624
Publication Date(Web):15 June 2014
DOI:10.1016/j.bmcl.2014.04.074
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, a series of novel hydrazone derivatives of podophyllotoxin, which is a naturally occurring aryltetralin lignan and isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum species, were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. Especially compounds 8i, 8j, 8t, and 8u showed the more potent insecticidal activity with the final mortality rates greater than 60%.
Co-reporter:Yanhua Zhang, Yuanyuan Yan, Suying Chen, Zhinan Gao, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 23) pp:5373-5376
Publication Date(Web):1 December 2014
DOI:10.1016/j.bmcl.2014.10.052
A new ‘naked-eye’ quinoline-based ‘reactive’ ratiometric fluorescent probe was prepared. The reactive stoichiometry of the probe with Hg2+ ion was 2:1. The probe exhibited high selectivity towards Hg2+ ion to other metal ions with a 410-fold increase in absorbance intensity ratio (A402/A340) in aqueous solution over a wide-range pH value (2–12), accompanied by a resonance color change from colorless to pale yellow visible to naked-eye.
Co-reporter:Xiaoyan Zhi, Chun Yang, Xiang Yu, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 24) pp:5679-5682
Publication Date(Web):15 December 2014
DOI:10.1016/j.bmcl.2014.10.081
To discover new natural-product-based insecticidal agents, a series of novel oxime derivatives of podophyllotoxin-based phenazines modified in the C, D and E rings of podophyllotoxin were prepared and tested as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. The steric configuration of IIIc was unambiguously confirmed by single-crystal X-ray diffraction analysis. Compounds IIIa–d, and IIIi exhibited an equal or higher insecticidal activity than toosendanin.
Co-reporter:Dr. Yuanyuan Yan;Rui Zhang;Xiang Yu ;Dr. Hui Xu
ChemPlusChem 2014 Volume 79( Issue 12) pp:1676-1680
Publication Date(Web):
DOI:10.1002/cplu.201402266
Abstract
Based on specific reactivity of the vinyloxy group to Hg2+ ions, a new ratiometric phenanthroimidazole-based fluorescent sensor, 2-(2-(vinyloxy)phenyl)-1 H-phenanthro[9,10-d]imidazole, is prepared. The selectivity of the probe toward Hg2+ ions is very high, and shows minimal interference from other commonly coexistent metal ions. The reactive stoichiometry of the probe with Hg2+ ion is 2:1. Its detection limit is evaluated and Hg2+ ions can be detected down to a lower limit of 2.5×10−8 M. Moreover, the Hg2+-promoted selective hydrolysis of a vinyloxy group of the probe is further confirmed by 1H NMR spectroscopy and mass spectrometry.
Co-reporter:Juanjuan Wang, Xiaoyan Zhi, Xiang Yu, and Hui Xu
Journal of Agricultural and Food Chemistry 2013 Volume 61(Issue 26) pp:6336-6343
Publication Date(Web):June 11, 2013
DOI:10.1021/jf4011033
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, a series of new deoxypodophyllotoxin-based phenazine analogues modified in their E-ring were prepared, and their structures were well characterized by 1H NMR, HRMS, ESI-MS, IR, optical rotation, and mp. The absolute steric configuration of one key isomer was unambiguously confirmed by X-ray crystallography. Their insecticidal activity was examined against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at the concentration of 1 mg/mL. All derivatives showed delayed insecticidal activity. Especially compound 9i, containing p-methoxybenzoylamnio at the C-9′ position of deoxypodophyllotoxin-based phenazine fragment, exhibited the most promising insecticidal activity with the final mortality rate of 72.4%. According to the symptoms of the tested M. separata, the derivatives likely displayed an antimolting hormone effect. In addition, preliminary structure–activity relationships were observed. These suggested that the proper length of the side chain of alkylacylamino might be important for their insecticidal activity, and introduction of the acylamino groups at the C-9′ position of deoxypodophyllotoxin-based phenazine fragment usually afforded more potent compounds than those containing the same ones at the C-10′ position. This will pave the way for further design, structural modification, and development of deoxypodophyllotoxin-based derivatives as insecticidal agents.
Co-reporter:Zhiping Che, Xiang Yu, Xiaoyan Zhi, Lingling Fan, Xiaojun Yao, and Hui Xu
Journal of Agricultural and Food Chemistry 2013 Volume 61(Issue 34) pp:8148-8155
Publication Date(Web):August 5, 2013
DOI:10.1021/jf4025079
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have prepared three series of novel 4α-(acyloxy)-2′(2′,6′)-(di)halogenopodophyllotoxin derivatives modified in the C and E rings of podophyllotoxin, which is a naturally occurring aryltetralin lignan isolated from the roots and rhizomes of Podophyllum hexandrum. Their structures were well characterized by 1H NMR, HRMS, ESI-MS, optical rotation, and mp. The stereochemical configurations of compounds 5s, 6b, 6d, and 7q were unambiguously confirmed by single-crystal X-ray diffraction. Their insecticidal activity was evaluated against the pre-third-instar larvae of oriental armyworm, Mythimna separata Walker, in vivo at a concentration of 1 mg/mL. These derivatives likely displayed the antimolting hormone effect. Among all the derivatives, especially compounds 5a, 5n, 7f, 7n, and 7w exhibited the most potent insecticidal activity with final mortality rates of 70% or so. This suggested that a chlorine or bromine atom introduced at the C2′ or C2′ and C6′ positions on the E ring of podophyllotoxin was necessary for obtaining the potent compounds. This will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.
Co-reporter:Yong Guo, Huan Qu, Xiaoyan Zhi, Xiang Yu, Chun Yang, and Hui Xu
Journal of Agricultural and Food Chemistry 2013 Volume 61(Issue 49) pp:11937-11944
Publication Date(Web):November 21, 2013
DOI:10.1021/jf404195m
A series of novel fraxinellone derivatives modified at the C-1 or C-8 position in the B ring were prepared as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata Walker at 1 mg/mL. Five key steric configurations of compounds 2, 3, and 8f,g,j were further determined by single-crystal X-ray diffraction. It was found that the kinds and the amount of the reduction products of fraxinellone were related to the molar ratio between the reduction agent Red-Al and the substrate fraxinellone. Among all of the derivatives, compounds 2 and 8i,j,o displayed more promising insecticidal activity than their precursors fraxinellone and toosendanin. The preliminary structure–activity relationships revealed that the lactone (B-ring) of fraxinellone contributed to the observed insecticidal activity; the double bond at the C-2 position of fraxinellone was not necessary for the insecticidal activity; conversion of the oxygen atom of carbonyl group on the lactone of fraxinellone to a sulfur one does not improve the insecticidal activity; introduction of electron-withdrawing groups on the phenyl ring of 8f, to the benzoyloxy series, could result in more potent compounds.
Co-reporter:Yuanyuan Yan, Zhiping Che, Xiang Yu, Xiaoyan Zhi, Juanjuan Wang, Hui Xu
Bioorganic & Medicinal Chemistry 2013 Volume 21(Issue 2) pp:508-513
Publication Date(Web):15 January 2013
DOI:10.1016/j.bmc.2012.11.005
A novel selective and sensitive fluorescence ‘on-off-on’ probe based on tetraphenylethylene (TPE) motif for sequential recognition of Fe3+ and Hg2+ in water has been developed. Especially the complex 6-Fe3+ could behave as a ‘turn on’ fluorescent sensor over a wide-range pH value for detection of Hg2+. The selectivity of this complex for Hg2+ over other heavy and transition metal ions is excellent, and its sensitivity for Hg2+ is at 2 ppb in water.
Co-reporter:Shuzhen He, Yonghua Shao, Lingling Fan, Zhiping Che, Hui Xu, Xiaoyan Zhi, Juanjuan Wang, Xiaojun Yao, and Huan Qu
Journal of Agricultural and Food Chemistry 2013 Volume 61(Issue 3) pp:618-625
Publication Date(Web):January 1, 2013
DOI:10.1021/jf305011n
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have synthesized three series of novel 4-acyloxy compounds derived from podophyllotoxin modified in the A and C rings, which is isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum hexandrum. Their insecticidal activity was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata in vivo. Compound 9g displayed the best promising insecticidal activity. It revealed that cleavage of the 6,7-methylenedioxy group of podophyllotoxin will lead to a less active compound and that the C-4 position of podophyllotoxin was the important modification location. A quantitative structure–activity relationship (QSAR) model was developed by genetic algorithm combined with multiple linear regression (GA-MLR). For this model, the squared correlation coefficient (R2) is 0.914, the leave-one-out cross-validation correlation coefficient (Q2LOO) is 0.881, and the root-mean-square error (RMSE) is 0.024. Five descriptors, BEHm2, Mor14v, Wap, G1v, and RDF020e, are likely to influence the biological activity of these compounds. Among them, two important ones are BEHm2 and Mor14v. This study will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.
Co-reporter:Zhiping Che, Shaoyong Zhang, Yonghua Shao, Lingling Fan, Hui Xu, Xiang Yu, Xiaoyan Zhi, Xiaojun Yao, and Rui Zhang
Journal of Agricultural and Food Chemistry 2013 Volume 61(Issue 24) pp:5696-5705
Publication Date(Web):May 20, 2013
DOI:10.1021/jf400536q
In continuation of our program aimed at the discovery and development of natural-product-based pesticidal agents, 54 novel N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives were prepared, and their structures were well characterized by 1H NMR, 13C NMR, HRMS, ESI-MS, and mp. Their nematicidal activity was evaluated against that of the pine wood nematode, Bursaphelenchus xylophilus in vivo. Among all of the derivatives, especially V-12 and V-39 displayed the best promising nematicidal activity with LC50 values of 1.0969 and 1.2632 mg/L, respectively. This suggested that introduction of R1 and R2 together as the electron-withdrawing substituents, R3 as the methyl group, and R4 as the phenyl with the electron-donating substituents could be taken into account for further preparation of these kinds of compounds as nematicidal agents. Six selected descriptors are a WHIM descriptor (E1m), two GETAWAY descriptors (R1m+ and R3m+), a Burden eigenvalues descriptor (BEHm8), and two edge-adjacency index descriptors (EEig05x and EEig13d). Quantitative structure–activity relationship (QSAR) studies demonstrated that the structural factors, such as molecular mass (a negative correlation with the bioactivity) and molecular polarity (a positive correlation with bioactivity), are likely to govern the nematicidal activities of these compounds. For this model, the correlation coefficient (R2training set), the leave-one-out cross-validation correlation coefficient (Q2LOO), and the 7-fold cross-validation correlation coefficient (Q27-fold) were 0.791, 0.701, and 0.715, respectively. The external cross-validation correlation coefficient (Q2ext) and the root-mean-square error for the test set (RMSEtest set) were 0.774 and 3.412, respectively. This study will pave the way for future design, structural modification, and development of indole derivatives as nematicidal agents.
Co-reporter:Yong Guo, Yuanyuan Yan, Xiaoyan Zhi, Chun Yang, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 11) pp:3382-3384
Publication Date(Web):1 June 2013
DOI:10.1016/j.bmcl.2013.03.083
Based on highly selective and irreversible Hg2+-promoted desulfurization reaction, a new and simple phenanthroimidazole-type sensor was prepared and exhibited high selectivity towards Hg2+ ion over other metal ions, accompanied by transformation of a weakly fluorescent thioamide moiety (colorless) to a highly fluorescent amide one (blue), with a 136-fold increase in fluorescent intensity in aqueous solution with a pH span 2.57–9.12.
Co-reporter:Chun Yang, Yonghua Shao, Xiaoyan Zhi, Qu Huan, Xiang Yu, Xiaojun Yao, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 17) pp:4806-4812
Publication Date(Web):1 September 2013
DOI:10.1016/j.bmcl.2013.06.099
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, four series of novel cholesterol-based hydrazone derivatives were synthesized, and their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. All the derivatives showed the better insecticidal activity than their precursor cholesterol. Quantitative structure–activity relationship (QSAR) model demonstrated that six descriptors such as RDF085v, Mor06u, Mor11u, Dv, HATS0v and H-046, are likely to influence the insecticidal activity of these compounds. Among them, two important ones are the Mor06u and RDF085v.
Co-reporter:Huan Qu, Xiang Yu, Xiaoyan Zhi, Min Lv, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 20) pp:5552-5557
Publication Date(Web):15 October 2013
DOI:10.1016/j.bmcl.2013.08.053
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, twenty-six new piperine-based hydrazone derivatives were synthesized from piperine, an alkaloid isolated from Piper nigrum Linn. The single-crystal structures of 6c, 6q and 6w were unambiguously confirmed by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 6b, 6i and 6r, the final mortality rates of which, at the concentration of 1 mg/mL, were 62.1%, 65.5% and 65.5%, respectively, exhibited more pronounced insecticidal activity compared to toosendanin at 1 mg/mL, a commercial botanical insecticide isolated from Melia azedarach. It suggested that introduction of the substituents at the C-2 position on the phenyl ring of the hydrazone derivatives was important for their insecticidal activity.
Co-reporter:Zhiping Che, Xiang Yu, Lingling Fan, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 20) pp:5592-5598
Publication Date(Web):15 October 2013
DOI:10.1016/j.bmcl.2013.08.044
Unexpected sequential E-ring dihalogenation of podophyllotoxin analogues is reported. It demonstrated that a chlorine/bromine atom was prior introduced at the C2′ position of podophyllotoxin, and the corresponding free rotation of E-ring around the C1–C1′ bond of 2′-chloro or 2′-bromopodophyllotoxin was restricted. When 2′-chloro or 2′-bromopodophyllotoxin reacted with N-chlorosuccinimide (NCS), the chlorine atom was regioselectively introduced at their C6′ position on the E-ring. Whereas 2′-chloro or 2′-bromopodophyllotoxin reacted with NBS, the bromine atom was regioselectively introduced at their C5 position on the B-ring. When 2′-chloropodophyllotoxin reacted with different carboxylic acids in the presence of BF3·Et2O, the steric effect of its E-ring for stereoselective synthesis of 4β-acyloxy-2′-chloropodophyllotoxin derivatives was observed. The insecticidal activity of 2′(2′,6′)-(di)halogen-substituted podophyllotoxin derivatives were evaluated with Mythimna separata Walker.
Co-reporter:Yong Guo, Lingling Fan, Juanjuan Wang, Chun Yang, Huan Qu, Hui Xu
Tetrahedron 2013 69(2) pp: 774-781
Publication Date(Web):
DOI:10.1016/j.tet.2012.10.073
Co-reporter:Dr. Yuanyuan Yan;Yanhua Zhang ;Dr. Hui Xu
ChemPlusChem 2013 Volume 78( Issue 7) pp:628-631
Publication Date(Web):
DOI:10.1002/cplu.201300150
Co-reporter:Yi Wang, Yonghua Shao, Yangyang Wang, Lingling Fan, Xiang Yu, Xiaoyan Zhi, Chun Yang, Huan Qu, Xiaojun Yao, and Hui Xu
Journal of Agricultural and Food Chemistry 2012 Volume 60(Issue 34) pp:8435-8443
Publication Date(Web):August 14, 2012
DOI:10.1021/jf303069v
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, 33 isoxazoline and oxime derivatives of podophyllotoxin modified in the C and D rings were synthesized and their structures were characterized by Proton nuclear magnetic resonance (1H NMR), high-resolution mass spectrometry (HRMS), electrospray ionization–mass spectrometry (ESI–MS), optical rotation, melting point (mp), and infrared (IR) spectroscopy. The stereochemical configurations of compounds 5e, 5f, and 9f were unambiguously determined by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of northern armyworm, Mythimna separata (Walker), in vivo. Compounds 5e, 9c, 11g, and 11h especially exhibited more promising insecticidal activity than toosendanin, a commercial botanical insecticide extracted from Melia azedarach. A genetic algorithm combined with multiple linear regression (GA–MLR) calculation is performed by the MOBY DIGS package. Five selected descriptors are as follows: one two-dimensional (2D) autocorrelation descriptor (GATS4e), one edge adjacency indice (EEig06x), one RDF descriptor (RDF080v), one three-dimensional (3D) MoRSE descriptor (Mor09v), and one atom-centered fragment (H-052) descriptor. Quantitative structure–activity relationship studies demonstrated that the insecticidal activity of these compounds was mainly influenced by many factors, such as electronic distribution, steric factors, etc. For this model, the standard deviation error in prediction (SDEP) is 0.0592, the correlation coefficient (R2) is 0.861, and the leave-one-out cross-validation correlation coefficient (Q2loo) is 0.797.
Co-reporter:Yong Guo, Yuanyuan Yan, Xiang Yu, Yi Wang, Xiao-Yan Zhi, Ying Hu, and Hui Xu
Journal of Agricultural and Food Chemistry 2012 Volume 60(Issue 28) pp:7016-7021
Publication Date(Web):June 22, 2012
DOI:10.1021/jf301734h
In continuation of a program aimed at the discovery and development of natural products-based insecticidal agents, two series of novel fraxinellone-based esters were synthesized by modification at the C-4 or C-10 position of fraxinellone and evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata in vivo. An efficient method for the stereoselective synthesis of 4α-hydroxyfraxinellone from fraxinellonone was developed, and the steric configuration of 6h was unambiguously confirmed by X-ray crystallography. Among 37 compounds, some derivatives displayed potent insecticidal activity; especially compounds 6h, 6q, 6t, and 7q showed more promising insecticidal activity than toosendanin, a commercial botanical insecticide derived from Melia azedarach. This suggested that introduction of the fluorine atom on the phenyl ring could lead to a more potent compound than one possessing chlorine or bromine. Meanwhile, introduction of the heterocyclic fragments at the C-4 or C-10 position of fraxinellone was essential for their insecticidal activity. This will pave the way for further design, structural modification, and development of fraxinellone as an insecticidal agent.
Co-reporter:Huiling Dai
Chinese Journal of Chemistry 2012 Volume 30( Issue 2) pp:267-272
Publication Date(Web):
DOI:10.1002/cjoc.201180481
Abstract
A series of new fluorescent chemosensors 5a–5e, composed of two aminonaphthalimide fluorophores and 2,6-bis((N-aminoalkyl)aminocarboxy)pyridines, were prepared, characterized, and their fluorescent properties towards heavy and transition metal (HTM) ions were investigated. Chemosensors 5c–5e exhibited high selectivity and sensitivity for Cu2+ ion over other HTM ions with fluorescent quenching (green to colourless). It clearly demonstrated that the length of the linkers (diamines) between the aminonaphthalimides and 2,6-dicarboxypyridine of 5a–5e was very important for their sensitivity and selectivity for Cu2+ ion over other HTM ions.
Co-reporter:Yong Guo, Yuan-Yuan Yan, Chun Yang, Xiang Yu, Xiao-Yan Zhi, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 17) pp:5384-5387
Publication Date(Web):1 September 2012
DOI:10.1016/j.bmcl.2012.07.058
In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, twenty-three new fraxinellone-based hydrazone derivatives were smoothly prepared from fraxinellone via regioselectively allylic oxidation in the presence of selenium dioxide or chromium trioxide under microwave irradiation and subsequent condensation with hydrazides or hydrazines. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 6d and 7a displayed the most pronounced insecticidal activity compared with toosendanin, a commercial botanical insecticide derived from Melia azedarach.An efficient route for the regioselectively allylic oxidation of fraxinellone was developed. Especially 6d and 7a exhibited the most pronounced insecticidal activity compared with toosendanin, a commercial botanical insecticide derived from Melia azedarach.
Co-reporter:Dr. Huiling Dai;Yuanyuan Yan;Yong Guo;Lingling Fan;Zhiping Che ;Dr. Hui Xu
Chemistry - A European Journal 2012 Volume 18( Issue 36) pp:11188-11191
Publication Date(Web):
DOI:10.1002/chem.201201604
Co-reporter:Ling-ling Fan;Zhi-ping Che;Rui Zhang;Xiang Yu;Xiao-yan Zhi
Molecular Diversity 2012 Volume 16( Issue 2) pp:415-421
Publication Date(Web):2012 May
DOI:10.1007/s11030-012-9370-5
A series of benzopyrano[3,4-b](N-arylsulfonyl) indole derivatives and benzopyrano[4,3-b](N-arylsulfonyl) indole derivatives were synthesized from 2- or 3-methylindole via intermolecular SN2 reaction and subsequent intramolecular palladium-catalyzed aryl–aryl coupling reaction for the first time. It was suggested that, besides using the Fischer cyclization, benzopyrano[4,3-b]indoles and benzopyrano[3,4-b]indoles could also be prepared via intermolecular SN2 reaction and sequential intramolecular palladium-catalyzed coupling reaction.
Co-reporter:Hui Xu, Ling-ling Fan
European Journal of Medicinal Chemistry 2011 Volume 46(Issue 5) pp:1919-1925
Publication Date(Web):May 2011
DOI:10.1016/j.ejmech.2011.02.035
A series of new 5,6-dihydro-indolo[1,2-a]quinoxaline derivatives has been prepared in moderate to excellent yields from 2-(indol-1-yl)phenylamines with aromatic aldehydes by an efficient and economical iron-catalyzed Pictet–Spengler reaction. Meanwhile, as compared with hymexazol, a commercially available agricultural fungicide at the concentration of 50 μg/mL, some 5,6-dihydro-indolo[1,2-a]quinoxalines exhibited promising antifungal activities in vitro against the phytopathogenic fungi, and might be considered as novel promising lead candidates for further design and synthesis of agricultural fungicides.17 novel 5,6-dihydro-indolo[1,2-a]quinoxalines were efficiently prepared, and some derivatives exhibited promising antifungal activities in vitro against the phytopathogenic fungi.Highlights► 5,6-Dihydro-indolo[1,2-a]quinoxalines were synthesized by a convenient, economic and efficient Pictet–Spengler cyclization reaction in the presence of FeCl3·6H2O. ► Their antifungal activities were evaluated against phytopathogenic fungi. ► Some compounds exhibited the promising and pronounced antifungal activities.
Co-reporter:Hui Xu, Ling-ling Fan
European Journal of Medicinal Chemistry 2011 Volume 46(Issue 1) pp:364-369
Publication Date(Web):January 2011
DOI:10.1016/j.ejmech.2010.10.022
A series of novel indole[1,2-c]-1,2,4-benzotriazine derivatives were obtained by a modified Sandmeyer reaction in the presence of tert-butylnitrite (t-BuONO). As compared with hymexazol, a commercially available agricultural fungicide, at the concentration of 50 μg/mL, two indole[1,2-c]-1,2,4-benzotriazines, 5h and 5k, exhibited the more promising and pronounced antifungal activities in vitro against five phytopathogenic fungi. It clearly demonstrated that introduction of appropriate substituents on the indolyl ring of indole[1,2-c]-1,2,4-benzotriazine (5a) would lead to the more potent derivatives.Two indole[1,2-c]-1,2,4-benzotriazine derivatives have been identified as potent antifungal agents and might be considered as novel promising lead candidates for further design and synthesis of agricultural fungicides.Research highlights► Indole[1,2-c]-1,2,4-benzotriazine derivatives were synthesized by a modified Sandmeyer reaction. ► Their antifungal activities were tested against phytopathogenic fungi. ► Two compounds exhibited the promising and pronounced antifungal activities.
Co-reporter:Hui Xu;Wen bin Yang ;Qin Wang
Chemical Biology & Drug Design 2011 Volume 78( Issue 5) pp:864-868
Publication Date(Web):
DOI:10.1111/j.1747-0285.2011.01212.x
To find more potent antifungal compounds, twenty 3-acylindole analogs were synthesized and bio-evaluated for their antifungal activities against seven phytopathogenic fungi. Structure–activity relationships investigations revealed that 4- or 6-methyl and 3-acetyl or propionyl groups were the important structural properties of 3-acylindoles for the activities. Especially 4-methyl-3-propionylindole, 12, displayed the more potent activities than hymexazol, a commercially available agricultural fungicide, and might be considered as a new promising lead candidate for further design and synthesis of agricultural fungicides.
Co-reporter:Hui Xu;Xiwen Zeng ;Huiling Dai
Chinese Journal of Chemistry 2011 Volume 29( Issue 10) pp:2165-2168
Publication Date(Web):
DOI:10.1002/cjoc.201180375
Abstract
A new fluorescent chemosensor based upon 1,8-naphthalimide and 8-hydroxyquinoline was synthesized, and its fluorescent properties in the presence of different metal cations (Hg2+, Ag+, Zn2+, Fe2+, Cd2+, Pb2+, Ca2+, Cu2+, Mg2+, and Ba2+) were investigated. It displayed fluorescence quenching with some heavy and transition metal (HTM) ions, and the quenching strongly depended on the nature of HTM ions.
Co-reporter:Hui Xu, Xiao Xiao
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 4) pp:1282
Publication Date(Web):15 February 2011
DOI:10.1016/j.bmcl.2011.01.009
Co-reporter:Hui Xu, Jun-Liang Zhang
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 7) pp:1974-1977
Publication Date(Web):1 April 2011
DOI:10.1016/j.bmcl.2011.02.031
In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, twelve 28-acyloxy derivatives of toosendanin (2a–l) were semisynthesized and preliminarily evaluated their activity against the pre-third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. Some compounds exhibited the potent insecticidal activity. Especially compounds 2c and 2j displayed the more promising insecticidal activity than their natural precursor, toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. In general, it indicated that the butanoyloxy or phenylacryloyloxy moiety at the 28-position of toosendanin was essential for the insecticidal activity.It indicated that the butanoyloxy or phenylacryloyloxy moiety at the 28-position of toosendanin was important for the insecticidal activity.
Co-reporter:Huiling Dai, Hui Xu
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 18) pp:5141-5144
Publication Date(Web):15 September 2011
DOI:10.1016/j.bmcl.2011.07.085
A water-soluble 1,8-naphthalimide-based fluorescent chemosensor 1, bearing two acetic carboxylic moieties, exhibited high selectivity and sensitivity for recognition of Hg2+ ion in water over other heavy and transition metal (HTM) ions with fluorescent enhancement. An increase in the fluorescent intensity at 562 nm was due to the formation of a 1:1 1−Hg2+ inclusion complex.A water-soluble 1,8-naphthalimide-based fluorescent chemosensor 1, by the formation of a 1:1 1−Hg2+ inclusion complexes, exhibited high selectivity and sensitivity for recognition of Hg2+ ion in water over other heavy and transition metal ions with fluorescent enhancement at 562 nm.
Co-reporter:Hui Xu, Jun-Liang Zhang
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 18) pp:5177-5180
Publication Date(Web):15 September 2011
DOI:10.1016/j.bmcl.2011.07.075
In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c′ and 9g′ exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxins might be important for the insecticidal activity.It preliminarily indicated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxins might be essential for the insecticidal activity.
Co-reporter:Hui Xu, Xiao Xiao, Xue-Fei Zhao, Yong Guo, Xiao-Jun Yao
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 13) pp:4008-4012
Publication Date(Web):1 July 2011
DOI:10.1016/j.bmcl.2011.05.004
Twenty-one 4α-acyloxy-2-chloropodophyllotoxin derivatives (5a–u), whose C-4 spatial configuration was mainly stereocontrolled by the configuration of C-2 chlorine atom, were unexpectedly prepared by the reaction of 2-chloropodophyllotoxin with carboxylic acids in the presence of BF3·Et2O. Compared with ordinary esterifications of carboxylic acids mediated by the condensation agent, for example, N,N’-diisopropylcarbodiimide (DIC), the present method made the procedure for the preparation of 4α-acyloxy-2-chloropodophyllotoxins more convenient, practical and easy. Meanwhile, the insecticidal activity of compounds 5a–u was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL.
Co-reporter:Dr. Hui Xu;Qingtian Wang ;Dr. Yong Guo
Chemistry - A European Journal 2011 Volume 17( Issue 30) pp:8299-8303
Publication Date(Web):
DOI:10.1002/chem.201100855
Co-reporter:Hui Xu, Xiwen Zeng
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 14) pp:4193-4195
Publication Date(Web):15 July 2010
DOI:10.1016/j.bmcl.2010.05.048
As compared with a commercially available agricultural fungicide hymexazol, some phenyl-azo phenol derivatives (e.g., 4a, 4b, 4f, 4n, 4q, 4u, and 4v) exhibited the more promising and pronounced antifungal activities in vitro against seven phytopathogenic fungi. It seemed that 4-((un)substituted phenylazo)-phenol and 4-((un)substituted phenylazo)-3-methylphenol might be considered as new lead structures for further design of agricultural fungicides.Among of all the compounds 4a–w, 4-((un)substituted phenylazo)-phenol (III) and 4-((un)substituted phenylazo)-3-methylphenol (IV) might be considered as new promising lead candidates for further design and synthesis of agricultural fungicides.
Co-reporter:Jun-Qiang Ran, Ning Huang, Hui Xu, Liu-Meng Yang, Min Lv, Yong-Tang Zheng
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 12) pp:3534-3536
Publication Date(Web):15 June 2010
DOI:10.1016/j.bmcl.2010.04.132
In continuation of our program aimed at the discovery and development of compounds with superior anti-human immunodeficiency virus type 1 (HIV-1) activity, 21N-arylsulfonyl-3-acetylindole analogs (2a–u) were synthesized and preliminarily evaluated as HIV-1 inhibitors in vitro. Among of all the analogs, several compounds exhibited significant anti-HIV-1 activity, especially N-phenylsulfonyl-3-acetyl-6-methylindole (2j) and N-(p-ethyl)phenylsulfonyl-3-acetyl-6-methylindole (2n) showed the most potent anti-HIV-1 activity with EC50 values of 0.36 and 0.13 μg/mL, and TI values of >555.55 and 791.85, respectively. It demonstrated that introduction of the acetyl group at the 3-position of N-arylsulfonyl-6-methylindoles could generally lead to the more potent analogs.It demonstrated that introduction of the acetyl group at the 3-position of N-arylsulfonyl-6-methylindoles could generally lead to the more potent analogs.
Co-reporter:Hui Xu, Xiao Xiao, Qing-tian Wang
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 17) pp:5009-5012
Publication Date(Web):1 September 2010
DOI:10.1016/j.bmcl.2010.07.050
In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 16 novel 4α-alkyloxy-2-chloropodophyllotoxin derivatives were semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Among all the tested derivatives, especially compounds 4b, 4e, 4g, and 4p exhibited more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach. Generally, it was obviously demonstrated that the length of straight-chain or branched-chain alkyloxy, and heteroatom-containing cycloalkyloxy at the C-4 position of 2-chloropodophyllotoxin were very important for the insecticidal activity.Some derivatives exhibited more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach. It was clearly demonstrated that the length of straight-chain or branched-chain alkyloxy, and heteroatom-containing cycloalkyloxy at the C-4 position of 2-chloropodophyllotoxin were very important for the insecticidal activity.
Co-reporter:Hui Xu, Juan-Juan Wang
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 8) pp:2500-2502
Publication Date(Web):15 April 2010
DOI:10.1016/j.bmcl.2010.02.108
Co-reporter:Hui Xu, Xiao-Qiang He
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 15) pp:4503-4506
Publication Date(Web):1 August 2010
DOI:10.1016/j.bmcl.2010.06.032
To discover the more potent analogs, 12 novel monomethyl phthalate derivatives of podophyllotoxin were synthesized and preliminarily tested against the pre-third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. Compounds 8e–i showed the higher insecticidal activity than podophyllotoxin. Especially 8g exhibited the most potent insecticidal activity compared with toosendanin, a commercially available insecticide derived from Melia azedarach. The structure–activity relationships demonstrated that trans-lactone, 4β-substitution, 2β-chlorine substitution, and 4′-methoxy group were the important structural properties of podophyllotoxins for good insecticidal activity.Trans-lactone, 4β-substitution, 2β-chlorine substitution, and 4′-methoxy group were the important structural properties of podophyllotoxins for good insecticidal activity.
Co-reporter:Hui Xu;Yangyang Wang
Chinese Journal of Chemistry 2010 Volume 28( Issue 1) pp:125-127
Publication Date(Web):
DOI:10.1002/cjoc.201090028
Abstract
An efficient synthesis of N-arylsulfonylindoles from indoles and arylsulfonyl chlorides in the presence of triethylbenzylammonium chloride (TEBA) and NaOH at room temperature is described.
Co-reporter:Hui Xu, Yang-Yang Wang
Bioorganic & Medicinal Chemistry Letters 2010 20(24) pp: 7274-7277
Publication Date(Web):
DOI:10.1016/j.bmcl.2010.10.084
Co-reporter:Hui Xu, Juanjuan Wang, Huijun Sun, Min Lv, Xuan Tian, Xiaojun Yao and Xing Zhang
Journal of Agricultural and Food Chemistry 2009 Volume 57(Issue 17) pp:7919-7923
Publication Date(Web):August 18, 2009
DOI:10.1021/jf9020812
By using podophyllotoxin as a phytoinsecticidal lead compound, 15 novel aromatic esters of 4′-demethyl-4-deoxypodophyllotoxin were semisynthesized and preliminarily tested for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo for the first time. Among all of the tested compounds, especially two compounds, 4m and 4o, containing a pyridinyl group, for which final corrected mortality rates against M. separata at 1 mg/mL were 62.9 and 59.2%, respectively, showed the most promising and pronounced insecticidal activity as compared with toosendanin, a commercial insecticide derived from Melia azedarach. The quantitative structure−activity relationships (QSAR) of compounds 4a−4o showed that the relative number of benzene rings and final heat of formation were very important descriptors to their insecticidal activity.
Co-reporter:Hui Xu, Xiao Xiao
Bioorganic & Medicinal Chemistry Letters 2009 Volume 19(Issue 18) pp:5415-5418
Publication Date(Web):15 September 2009
DOI:10.1016/j.bmcl.2009.07.116
By using podophyllotoxin as a lead compound, eight novel esters of 2-chloropodophyllotoxin were designed, semisynthesized, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo for the first time. Among all the tested compounds, especially three esters of 2-chloropodophyllotoxin 8a, 8c, and 8g, and one intermediate 6 showed more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach.
Co-reporter:Hui Xu, Yang Chen
Ultrasonics Sonochemistry 2008 Volume 15(Issue 6) pp:930-932
Publication Date(Web):September 2008
DOI:10.1016/j.ultsonch.2008.03.001
Mandelic acid was synthesized from benzaldehyde with chloroform in a 81% yield at 60 °C for 2 h by using triethylbenzylammonium chloride (TEBA) and poly(ethylene glycol)-800 (PEG-800) as a complex phase transfer catalyst under ultrasonic irradiation. The main advantages of this present method are that the reaction time is much shorter and the yield is higher than those of the classical method. p-Methoxymandelic acid was also obtained in a 84% yield under the same reaction conditions.
Co-reporter:Hui XU;Fei YE ;Hui-Ling DAI
Chinese Journal of Chemistry 2008 Volume 26( Issue 8) pp:1465-1468
Publication Date(Web):
DOI:10.1002/cjoc.200890266
Abstract
In an ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate), an efficient anhydrous K2CO3-mediated tandem deprotection of (un)substituted phenyl methanesulfonates and nucleophilic aromatic substitution reactions (SNAr) with activated (un)substituted phenyl halides to synthesize unsymmetrical diphenyl ethers has been described. The solvent could be recycled without loss of any efficiency, and the procedure was quite convenient, practical and environmentally benign.
Co-reporter:Jiulin Huang, Ming Xu, Shaochen Li, Jiani He, Hui Xu
Bioorganic & Medicinal Chemistry Letters (1 February 2017) Volume 27(Issue 3) pp:
Publication Date(Web):1 February 2017
DOI:10.1016/j.bmcl.2016.12.026
Podophyllotoxin is a naturally occurring non-alkaloid toxin isolated from the roots and rhizomes of Podophyllum peltatum and P. hexandrum. In continuation of our program aimed at the discovery and development of natural product-based insecticides, two series of ester derivatives of 4′-demethoxyepipodophyllotoxin/2′-chloro-4′-demethoxyepipodophyllotoxin were prepared. The structures of the target compounds were well characterized by 1H NMR, IR, optical rotation and mp. The precise three-dimensional structural information of 8j was further determined by single-crystal X-ray diffraction. Their insecticidal activity was tested against Mythimna separata Walker. These compounds showed delayed insecticidal activity. Among all derivatives, some compounds showed more potent insecticidal activity than toosendanin against M. separata; especially compounds 8k and 9k exhibited the most potent activity with the final mortality rates of 71.4%. Their structure–activity relationships were discussed.