Co-reporter:Qi Chen, Ji-Wei Zhang, Lu-Lu Chen, Jun Yang, ... Qing Yang
Chinese Chemical Letters 2017 Volume 28, Issue 6(Volume 28, Issue 6) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/j.cclet.2017.03.030
Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5 μmol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum, Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides.Download high-res image (140KB)Download full-size imageAccording to the structure of chitin synthase donor substrate, UDP-GlcNAc, as well as the modelled structure of the bacterial chitin synthase NodC, a novel scaffold with chitin synthase inhibitory activity and antifungal activity was developed.
Co-reporter:Gao-Fei Xu, Xin-Ling Yang, Peng Lei, Xi-li Liu, Xue-Bo Zhang, Yun Ling
Chinese Chemical Letters 2016 Volume 27(Issue 4) pp:555-558
Publication Date(Web):April 2016
DOI:10.1016/j.cclet.2016.01.045
A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI) or elemental analysis, 13C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 μmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure–activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.The title compounds, 2,6-dimethylmorpholine-containing daphneolone analogs, were designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. Preliminary bioassay showed that these compounds exhibited moderate to good fungicidal activities. Between the two isomers of target compounds, the fungicidal activities of the isomer with cis-2,6-dimethylmorpholine were better than the isomer with trans-2,6-dimethylmorpholine moiety.
Co-reporter:Peng Lei, Yan Xu, Juan Du, Xin-Ling Yang, Hui-Zhu Yuan, Gao-Fei Xu, Yun Ling
Bioorganic & Medicinal Chemistry Letters 2016 Volume 26(Issue 10) pp:2544-2546
Publication Date(Web):15 May 2016
DOI:10.1016/j.bmcl.2016.03.085
To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.
Co-reporter:Ruilong Xie, Hua Fu and Yun Ling
Chemical Communications 2011 vol. 47(Issue 31) pp:8976-8978
Publication Date(Web):05 Jul 2011
DOI:10.1039/C1CC13516C
An efficient copper-catalyzed method for N-arylation of amines has been developed with part-per-million catalyst loadings at room temperature under air. Reactions of substituted (E)-1-(2-halophenyl)alkanone oximes with aliphatic amines or aromatic amines provided the N-arylation products in good to excellent yields.
Co-reporter:Shaoxiang Yang;Tieniu Kang;Changhui Rui;Xinling Yang;Yufeng Sun;Zining Cui
Chinese Journal of Chemistry 2011 Volume 29( Issue 11) pp:2394-2400
Publication Date(Web):
DOI:10.1002/cjoc.201180409
Abstract
Three series of novel 1,5-diphenyl-1-pentanone derivatives were designed and synthesized. Their structures were characterized by IR, 1H NMR techniques, and elemental analysis. The insecticidal activities of the new compounds were preliminarily evaluated. The bioassay results indicated that the compounds X11–X30 displayed better aphicidal activity against Aphis gossypii than compounds X1–X10 and the lead compound (E)-1,5-diphenyl-1-penten-1-one (A). The inhibitory rates of compounds X6 and X29 were 100% against Plutella xylostella (L.) at 600 mg·L−1. Compounds X12, X13, X19, X24, X25, X26 and X27 showed higher insecticidal activity against Tetranychus cinnabarinus (Boisduval) at 600 mg·L−1 than the lead compound (A).
Co-reporter:Ying Li, Bao-Ju Li, Yun Ling, Hong-Jian Miao, Yan-Xia Shi and Xin-Ling Yang
Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 5) pp:3037-3042
Publication Date(Web):February 12, 2010
DOI:10.1021/jf9043277
Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, 1H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus, but most compounds exhibited good fungicidal activities against Corynespora cassiicola, Thanatephorus cucumeris, Botrytis cinerea, and Fusarium oxysporum. In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.
Co-reporter:Xichen Li;Xinling Yang;Zining Cui;Ying Li;Hongwu He
Chinese Journal of Chemistry 2010 Volume 28( Issue 7) pp:1233-1239
Publication Date(Web):
DOI:10.1002/cjoc.201090214
Abstract
Diacylhydrazines have been found as molting hormone analogs since RH-5849 was reported as the first nonsteroidal ecdysone agonist in 1988. Optimizations on diacylhydrizines with benzoheterocycle containing oxygen were widely explored in recent years. In order to find novel compounds with high bioactivity, a series of mono- (I) and di-acylhydrazine (II) derivatives containing furan were designed and synthesized. Their structures were confirmed by 1H NMR, IR, elemental analyses and single crystal X-ray diffraction analyses (II7). The bioassay results showed that some of the mono-acylhydrazine (I) derivatives exhibited good larvicidal activity against Culex pipiens pallens at 10 mg/L and better than those of di-acylhydrazines (II). Generally, the anti-tumor activity of di-acylhydrazines (II) was better than that of mono-acylhydrazines (I).
Co-reporter:Zining Cui;Li Zhang;Juan Huang;Xinling Yang
Chinese Journal of Chemistry 2010 Volume 28( Issue 7) pp:1257-1266
Publication Date(Web):
DOI:10.1002/cjoc.201090218
Abstract
42 novel diacylhydrazine derivatives containing furan were synthesized by the reaction of 5-substituted phenyl-2-furoyl chloride with substituted benzohydrazide in anhydrous dichloromethane under reflux. Their structures were confirmed by IR, 1H NMR, MS and elemental analysis. Insecticidal and antitumor activity of these new compounds was evaluated. The preliminary bioassays showed that the target compounds exhibited larvicidal activity to the Mythimna separate, some of them exhibited good or moderate larvicidal activity. At the concentration of 0.1%, compounds I2, I4, I5, and III1 showed 95.0%, 90.0%, 95.0% and 95.0% larvicidal activity to Mythimna separate respectively. Some compounds such as I2, I4, I5 and III1 showed the typical IGRs' activity, which could induce the larvae premature, abnormal, and lethal larval molt. Results of anticancer activity indicated that some compounds exhibited potential activity against some human cancer cell lines, for example, I1 and IV showed good activity to the BGC-823 and the inhibitory rates were 60.86% and 61.94% respectively at 10 µmol/L.
Co-reporter:Gangyi Shen;Jian Cui;Xinling Yang
Journal of Separation Science 2009 Volume 32( Issue 1) pp:79-87
Publication Date(Web):
DOI:10.1002/jssc.200800477
Abstract
A new β-CD derivative, heptakis [2,6-di-O-pentyl-3-O-(4′-chloro-5′-pyridylmethyl)]-β-CD, was synthesized by the selective introduction of a pyridyl group on the 3-positions of β-CD. The chromatographic properties of the pyridyl β-CD derivative were studied by using it as the stationary phase in capillary GC. The polarity of the prepared stationary phase was moderate, and the separation results demonstrated that the prepared stationary phase possessed excellent separation ability and chiral recognition for a wide range of analytes. Not only the aromatic positional isomers, such as o-, m-, p-xylene and α-, β-naphthol isomers, but also some compounds with multi-stereogenic centers, such as n-(1-methylpropyl)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxamide and n-(1-methylpropyl)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxamide with three stereogenic centers including eight configurational isomers, were successfully separated. The results also indicated that the polarity of the β-CD derivative, and the hydrogen bonding between the β-CD derivative, and the analytes had a very important effect on separation.
Co-reporter:Ruilong Xie, Hua Fu and Yun Ling
Chemical Communications 2011 - vol. 47(Issue 31) pp:NaN8978-8978
Publication Date(Web):2011/07/05
DOI:10.1039/C1CC13516C
An efficient copper-catalyzed method for N-arylation of amines has been developed with part-per-million catalyst loadings at room temperature under air. Reactions of substituted (E)-1-(2-halophenyl)alkanone oximes with aliphatic amines or aromatic amines provided the N-arylation products in good to excellent yields.