BaoLin Li

Name: 李宝林; BaoLin Li

Organization: Shaanxi Normal University

Department: Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, and School of Chemistry and Materials Science

Title: Professor

Chemicals
References

Novel 4-arylaminoquinazoline derivatives with (E)-propen-1-yl moiety as potent EGFR inhibitors with enhanced antiproliferative activities against tumor cells

Co-reporter:Li Chen, Yaling Zhang, Juan Liu, Weijia Wang, Xiabing Li, Lijun Zhao, Wei Wang, Baolin Li

European Journal of Medicinal Chemistry 2017 Volume 138(Volume 138) pp:

Publication Date(Web):29 September 2017

DOI:10.1016/j.ejmech.2017.06.023

•A series of novel 4-(4-(E)-(propen-1-yl)phenylamino)quinazoline derivatives were designed and synthesized.•Most synthesized compounds exhibited good antiproliferative activities against human tumor cells.•Molecular docking suggested that the binding mode of 6e with EGFR was similar to gefitinib, but different from lapatinib.•6e can significantly suppress the phosphorylation of EGFR and its downstream signaling proteins in tumor cells.A series of novel 4-anilinoquinazoline derivatives with (E)-propen-1-yl moiety were designed, synthesized and evaluated for biological activities in vitro. Most compounds exhibited highly antiproliferative activities against all tested tumor cell lines including A431, A549, NCI-H1975 and SW480 cells. Especially, compound 6e not only presented strong antiproliferative activities against the tested four tumor cell lines (IC50 of 1.35, 8.83, 5.53 and 6.08 μM, respectively) which expressed wild type or L858R/T790M double mutant epidermal growth factor receptor (EGFR), but also showed potent inhibitory activity against wild type EGFR (IC50 = 20.72 nM). The result of molecular docking with EGFR suggested the binding mode of 6e was similar to gefitinib, but different from lapatinib. Additionally, western blot analysis showed that 6e inhibited the phosphorylation of EGFR and its downstream signaling proteins in lung cancer cells. The work could be very useful starting point for developing a new series of tyrosine kinase inhibitors targeting EGFR.Download high-res image (218KB)Download full-size image

Synthesis and in vitro biological evaluation of novel quinazoline derivatives

Co-reporter:Yaling Zhang, Ying Zhang, Juan Liu, Li Chen, Lijun Zhao, Baolin Li, Wei Wang

Bioorganic & Medicinal Chemistry Letters 2017 Volume 27, Issue 7(Issue 7) pp:

Publication Date(Web):1 April 2017

DOI:10.1016/j.bmcl.2017.02.027

A series of novel 4-arylamino-6-(5-substituted furan-2-yl)quinazoline derivatives were designed, synthesized and evaluated on biological activities in vitro. Compound 2a, 3a and 3c exhibited highly anti-proliferation activities on all tested tumor cell lines including SW480, A549, A431 and NCI-H1975 cells. Especially, compound 2a not only exhibited strong anti-proliferation activities against the tumor cell lines which expressed wild type or mutant EGFRL858R/T790M, but also showed the most potent inhibitory activity toward wild type EGFR (IC50 = 5.06 nM). The result of docking with EGFR suggested the binding mode of 2a was similar to that of lapatinib. While Western-blot analyses showed 2a obviously inhibited the activation of EGFR, Akt and Erk1/2 in lung cancer cells at indicated concentration. It is believed that this work would be very useful for developing a new series of TKIs targeting EGFR.Download high-res image (84KB)Download full-size image

Quinazoline-1-deoxynojirimycin hybrids as high active dual inhibitors of EGFR and α-glucosidase

Co-reporter:Yaling Zhang, Hongliang Gao, Renjie Liu, Juan Liu, Li Chen, Xiabing Li, Lijun Zhao, Wei Wang, Baolin Li

Bioorganic & Medicinal Chemistry Letters 2017 Volume 27, Issue 18(Issue 18) pp:

Publication Date(Web):15 September 2017

DOI:10.1016/j.bmcl.2017.08.035

A series of novel quinazoline-1-deoxynojirimycin hybrids were designed, synthesized and evaluated for their inhibitory activities against two drug target enzymes, epidermal growth factor receptor (EGFR) tyrosine kinase and α-glucosidase. Some synthesized compounds exhibited significantly inhibitory activities against the tested enzymes. Comparing with reference compounds gefitinib and lapatinib, compounds 7d, 8d, 9b and 9d showed higher inhibitory activities against EGFR (IC50: 1.79–10.71 nM). Meanwhile the inhibitory activities of 7d, 8d and 9c against α-glucosidase (IC50 = 0.14, 0.09 and 0.25 µM, respectively) were obvious higher than that of miglitol (IC50 = 2.43 µM), a clinical using α-glucosidase inhibitor. Interestingly, compound 9d as a dual inhibitor showed high inhibitory activity to EGFRwt tyrosine kinase (IC50 = 1.79 nM), also to α-glucosidase (IC50 = 0.39 µM). The work could be very useful starting point for developing a new series of enzyme inhibitors targeting EGFR and/or α-glucosidase.Download high-res image (88KB)Download full-size image

A novel sensor for the detection of alkaline phosphatase activity based on the self-assembly of Eu3+-doped oxide nanoparticles and heptamethine cyanine dye

Co-reporter:Ben Hao Li, Ya Ling Zhang, Fan Shi Li, Wei Wang, Juan Liu, Min Liu, Yi Cui, Xia Bing Li, Bao Lin Li

Sensors and Actuators B: Chemical 2016 Volume 233() pp:479-485

Publication Date(Web):5 October 2016

DOI:10.1016/j.snb.2016.04.102

•A self-assemblage of Y0.6Eu0.4VO4 nanoparticle (NP) and cyanine dye was firstly constructed and used as an alkaline phosphatase (ALP) sensor.•With the help of phosphate group, p-Cy7-A was captured on NP to form FRET by self-assembling in situ.•This sensor can very well respond to the amount and activity of ALP and its inhibitor.A non-fluorescent self-assemblage of Y0.6Eu0.4VO4 nanoparticle (NP) and heptamethine cyanine dye bearing phosphate group p-Cy7-A, NP-p-Cy7-A, was the first constructed and used as an alkaline phosphatase (ALP) sensor. Herein, Y0.6Eu0.4VO4 NP and new synthesized p-Cy7-A were employed respectively as donor and acceptor of Fluorescence Resonance Energy Transfer. With the help of phosphate group, p-Cy7-A as a dark quencher was captured on Y0.6Eu0.4VO4 NP surface to form non-fluorescent NP-p-Cy7-A in situ. The disintegration of NP-p-Cy7-A was triggered by the removal of phosphate group in p-Cy7-A catalyzed by ALP, and released fluorescent Y0.6Eu0.4VO4 NP. Thus NP-p-Cy7-A assemblage as a selective and sensitive sensor can very well responded to the amount and activity of ALP by measuring the fluorescent intensity at 620 nm (excited at 270 nm). This sensor can not only accurately measure the concentration of ALP (0.03–1.65 U/mL), but also be applied to detect the activity of ALP and screen its inhibitor by a simple mix-and-measure manner.

Sulfonated carbon nanocage as a catalyst for the per-O-acetylation of carbohydrates

Co-reporter:Bao Lin Li;Bo Zhang;Qi Hua Zhang;Yuan Wei Rong;Zhuan Xin Wan

Kinetics and Catalysis 2014 Volume 55( Issue 2) pp:233-236

Publication Date(Web):2014 March

DOI:10.1134/S0023158414020037

We report an efficient per-O-acetylation of carbohydrates. The use was made of the sulfonated carbon nanocage with high specific surface area and uniform mesoporous structure as a recyclable heterogeneous catalyst. This protocol eliminates the need to involve pyridine and provides products in good to excellent yields.

Phosphotungstic acid supported on mesoporous carbon as a catalyst for the oxidation of benzyl alcohol

Co-reporter:Bao Lin Li;Jiang Li;Xiao Mei Wang;Zhuan Xin Wan

Kinetics and Catalysis 2013 Volume 54( Issue 1) pp:69-75

Publication Date(Web):2013 January

DOI:10.1134/S0023158413010102

Phosphotungstic acid (PTA) was successfully supported on synthesized mesoporous carbon (MC) through impregnating method to yield a series of PTA/MC catalysts, the content of PTA from 16 to 43 wt %. The catalysts were characterized by FTIR spectroscopy, X-ray diffraction, N2 adsorption-desorption isotherm tests and transmission electron microscopy. The characterization data revealed that intact Keggin ion of PTA is kept in the support, and PTA is located equably inside the pores of MC. The catalytic activities of these catalysts were tested in selective oxidation of benzyl alcohol to benzaldehyde using 30% hydrogen peroxide as oxidant. The results indicated that 28 wt % PTA/MC catalyst with high specific surface area (474 m2/g) and uniform pore size (6.4 nm) possess the best catalytic activity (conversion of 82.6% and selectivity of 94.0%) among all prepared catalysts.

A wormhole-structured mesoporous carbon with superior adsorption for dyes

Co-reporter:Jiang Tao Li, Bao Lin Li, Hui Chun Wang, Xiao Bing Bian, Xiao Mei Wang

Carbon 2011 Volume 49(Issue 6) pp:1912-1918

Publication Date(Web):May 2011

DOI:10.1016/j.carbon.2011.01.016

A series of large-pore mesoporous carbon materials with a three-dimensional wormhole framework structure were synthesized by nanocasting using mesoporous silica as a hard template. Samples of hard-template mesoporous silica with pore diameters from 3.08 to 6.43 nm, pore volumes from 0.59 to 1.02 cm3 g−1 and surface areas from 832 to 579 m2 g−1 were prepared from tetraethyl orthosilicate as the silica source and ionic liquid 1-butyl-3-methylimidazolium bromide as structure-directing agent through hydrothermal treatment at different temperatures (110–150 °C) followed by calcining at 550 °C. Subsequently, carbon materials with large pore diameters (2.76–6.70 nm), pore volumes (0.74–2.10 cm3 g−1) and high surface areas (1074–1276 m2 g−1) were synthesized using the various mesoporous silicas synthesized at the different hydrothermal temperatures as a hard-template. The carbon material obtained at a hydrothermal temperature of 150 °C possesses outstanding adsorbility for amaranth and methylene blue dyes.

Direct synthesis of mesoporous carbon from the carbonization of hydroxypropyl-β-cyclodextrin/silica composite and its catalytic performance

Co-reporter:Hui Chun Wang, Bao Lin Li, Jiang Tao Li, Pei Lin, Xiao Bing Bian, Jiang Li, Bo Zhang, Zhuan Xin Wan

Applied Surface Science 2011 Volume 257(Issue 9) pp:4325-4330

Publication Date(Web):15 February 2011

DOI:10.1016/j.apsusc.2010.12.051

Abstract

A simple and efficient route is reported for the synthesis of mesoporous carbon materials by directly carbonizing hydroxypropyl-β-cyclodextrin-silica composites. The resulting carbon materials, with uniform wormlike mesoporous structure and certain degree graphitic phase characteristics in porous wall, possess narrow pore size distribution, high surface area (>1000 m² g⁻¹) and pore volume (>1.2 cm³ g⁻¹). It is worth mentioning that the carbon materials have high catalytic activity for the reduction of p-nitrotoluene using hydrazine hydrate as the reducing agent; moreover, the catalytic activity is not reduced notably after being reused for six times.

Synthesis of Sulfonated Carbon Nanocage and Its Performance as Solid Acid Catalyst

Co-reporter:Pei Lin;Jiangtao Li;Huichun Wang;Xiaobing Bian

Catalysis Letters 2011 Volume 141( Issue 3) pp:459-466

Publication Date(Web):2011 March

DOI:10.1007/s10562-010-0526-6

A carbon nanocage material (CKT) was first successfully sulfonated by introducing sulfophenyl groups on the surface of pore channels through benzenesulfonic acid-containing aryl radical in situ generated from the reaction of 4-aminobenzenesulfonic acid and isoamyl nitrite in water. The sulfonated carbon nanocage material (S-CKT) was characterized by Fourier transform infrared spectroscopy, transmission electron microscopy, powder small-angle X-ray diffraction and nitrogen sorption measurements. The results showed that the S-CKT still possess the high specific surface area (787 m2/g) and uniform mesoporous (pore diameter 4.7 nm) structures, although the structure of S-CKT is slightly disorder, compared with its unsulfonated precursor. S-CKT, as a carbon-based solid acid catalyst, showed good catalytic performance and reusability in the cross-Aldol condensation of ketones with aromatic aldehydes under solvent-free condition.

Low temperature strategy to synthesize high surface area mesoporous hydroxypropyl-β-cyclodextrin-based silicas via benign template removal

Co-reporter:Hui Chun Wang, Jiang Tao Li, Pei Lin, Xia Bing Li, Xiao Bing Bian, Xiao Mei Wang, Bao Lin Li

Microporous and Mesoporous Materials 2010 Volume 134(1–3) pp:175-180

Publication Date(Web):October 2010

DOI:10.1016/j.micromeso.2010.05.023

We report in the present paper the preparation of mesoporous silica materials from hydroxypropyl-β-cyclodextrin-silica hybrid via ammonium perchlorate oxidation method to remove organic templates at relatively low temperature (⩽100 °C). The results from IR and nitrogen adsorption show that the template-free silica product obtained after efficient cyclodextrin removal at 60 °C for 12 h in a Teflon autoclave has richer surface silanol groups and a higher surface area (849 m2 g−1) than the calcinated sample. XRD analysis and TEM measurement show that these silica materials have a disordered wormlike mesostructure. This study provides an easy, cheap and useful method for a large-scale preparation of mesoporous silica materials at low temperature.

Enantioselective Aldol Reaction of -Ketoester and Cyclopentaone Catalyzed by L-Proline

Co-reporter:Jiming Xiang

Chinese Journal of Chemistry 2010 Volume 28( Issue 4) pp:617-621

Publication Date(Web):

DOI:10.1002/cjoc.201090122

Abstract

A concise and enantioselective synthesis of (S)-ethyl 2-cyclopentyl-2-hydroxy-2-arylacetate, a key intermediate for the muscarinic receptor, is reported. The tertiary stereogenic center was constructed with good stereoselectivity through the L-proline-catalyzed direct asymmetric aldol reaction of ethyl arylglyoxylate and cyclopentanone. The carbonyl of the condensation product was reduced using a modified Clemmensen reaction which provided an easier workup and was more environmentally acceptable. The enantioselectivity of the aldol reactions was between 58.3%–93.2%, which means that the stereoselective is efficient in controlling configuration of reaction product.

The Stereoselective Synthesis of 2-Aryl-2-hydroxybutanoic Acid via Menthyl Chiral Auxiliaries

Co-reporter:Ji-Ming Xiang;Bao-Lin Li

Helvetica Chimica Acta 2010 Volume 93( Issue 10) pp:2015-2022

Publication Date(Web):

DOI:10.1002/hlca.201000024

Abstract

In the presence of titanium(IV) tetraethoxide ((EtO)₄Ti), menthyl arylglyoxylates are prepared by transesterification of ethyl arylglyoxylates and natural (−)-(1R,2S,5R)-menthol. Using menthyl as a chiral auxiliary, the corresponding novel (R)-menthyl 2-aryl-2-hydroxybutanoates are synthesized by the addition of Et₂Zn with menthyl arylglyoxylates. The structures of the products are characterized by IR and ¹H- and ¹³C-NMR spectroscopy, mass spectrometry, and elemental analysis. The diastereoselectivities are analyzed by HPLC. The addition reactions are completed with good yields and high diastereoisomeric excess (de up to 95%), and, after hydrolysis, the (R)-2-aryl-2-hydroxybutanoic acids are obtained with high optical purities.

Synthesis of PEG derivatives bearing aminophenyl and their application for liquid-phase synthesis of water-soluble unsymmetrical cyanine dyes

Co-reporter:Lin-Ling Jiang, Bao-Lin Li, Feng-Ting Lv, Li-Fang Dou, Liu-Chang Wang

Tetrahedron 2009 65(27) pp: 5257-5264

Publication Date(Web):

DOI:10.1016/j.tet.2009.04.086

Chiral resolutions of (9-anthryl)methoxyacetic acid and (9-anthryl)hydroxyacetic acid by capillary electrophoresis

Co-reporter:Bao-Lin Li;Zhen-Guo Zhang;Li-Li Du;Wei Wang

Chirality 2008 Volume 20( Issue 1) pp:35-39

Publication Date(Web):

DOI:10.1002/chir.20485

Abstract

The resolutions of (9-anthryl)methoxyacetic acid (9AMAA) and (9-anthryl)hydroxyacetic acid (9AHAA) were performed by capillary electrophoresis using hydroxypropyl-β-cyclodextrin (HP-β-CD) as a chiral selector. Various factors affecting migration time and resolutions of these compounds were investigated with a run voltage of 20 kV, column temperature 20°C and 20 mM Tris-H₃PO₄ buffer (pH 6.5) containing 5 mM HP-β-CD for 9AMAA, or 10 mM HP-β-CD for 9AHAA, (±)-9AMAA and (±)-9AHAA were successfully separated at Rs 3.27 and 1.92, respectively. Chirality, 2007. © 2007 Wiley-Liss, Inc.

Configuration, conformation and crystal structure of rabdosianin b

Co-reporter:Bao Lin Li;Yuan Jiang Pan;Jin Li;Ling Tong;Kai Bei Yu

Crystal Research and Technology 2005 Volume 40(Issue 8) pp:

Publication Date(Web):6 JUN 2005

DOI:10.1002/crat.200410436

Rabdosianin B, 7,20-epoxy-7β-hydroxy-1α,6β,11α,15β-tetraacetoxy-ent-kaur-16-ene, C₂₈H₃₈O₁₀, was the first isolated from Isodon henryi. It consists of three six-membered rings A, B, C and one five-membered ring D. The fused-ring system A, B and C are in chair, boat and chair conformations, respectively, and ring D is in an envelope conformation, on the basis of NMR and X-ray diffraction analysis. The crystal of rabdosianin B is in orthorhombic crystal system with space group P2₁2₁2₁, lattice constants: a = 9.969(1) Å, b = 15.400(3) Å, and c = 17.624(3) Å, Z = 4. (© 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim)

Two New C(20)-Oxygenated ent-Kaurene Diterpenoids from Isodon henryi

Co-reporter:Weijie Pan;Yuanjang Pan

Helvetica Chimica Acta 2001 Volume 84(Issue 11) pp:3418-3422

Publication Date(Web):6 DEC 2001

DOI:10.1002/1522-2675(20011114)84:11<3418::AID-HLCA3418>3.0.CO;2-L

Two new C(20)-oxygenated ent-kaurene diterpenoids, taibaihenryiins A (1) and B (2), along with five known compounds, shikokianin (3), longikaurin D, 2α-hydroxyursolic acid, longikaurin F, and lasiodin, were isolated from the EtOH extract of the leaves and tender branches of Isodon henryi (Hemsl.) Kudo. The structures of the new compounds were determined as 11α-acetoxy-7,20-epoxy-1α,6β,7β-trihydroxy-ent-kaur-16-en-15-one (1) and 7,20-epoxy-3β,6β,7β,11α-tetrahydroxy-ent-kaur-16-en-15-one (2) on the basis of detailed spectroscopic analyses.

Enmein type diterpenoids from Isodon japonica

Co-reporter:Baolin Li, Xianhua Tian

Phytochemistry 2001 Volume 58(Issue 4) pp:543-546

Publication Date(Web):October 2001

DOI:10.1016/S0031-9422(01)00245-X

Two enmein type diterpenoids, taibaijaponicains A and B, were isolated from the ethanol extract of the leaves and branches of Isodon japonica. Their structures are designated as 6β,11α-dihydroxy-16α-methoxymethyl-6,20-epoxy-6,7-seco-ent-kaur-15-one-1,7-olide and 3β-acetoxy-6β,11α-dihydroxy-16α-methoxymethyl-6,20-epoxy-6,7-seco-ent-kaur-15-one-1,7-olide, respectively, on the basis of detailed spectroscopic analyses.Two enmein type diterpenoids, taibaijaponicains A and B, were isolated from Isodon japonica. Their structures were designated as 6β,11α-dihydroxy-16α-methoxymethyl-6,20-epoxy-6,7-seco-ent-kaur-15-one-1,7-olide (1) and 3β-acetoxy-6β,11α-dihydroxy-16α-methoxymethyl-6,20-epoxy-6,7-seco-ent-kaur-15-one-1,7-olide (2) on the basis of detailed spectroscopic analyses.