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Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle

文献类型：期刊论文

作者Li Yingjun1; Lin Ledi1; Liu Jihong2; Gao Lixin3; Sheng Li3; Jin Kun4; Liu Xuejie1; Yang Hongjing1; Li Jia3
刊名CHINESE JOURNAL OF ORGANIC CHEMISTRY
出版日期2021-09-01
卷号41期号:9页码:3593-3607
ISSN号0253-2786
关键词PTP1B inhibitor carbazole N-actylhydrazone synthesis molecular docking
DOI10.6023/cjoc202105032
通讯作者Li Yingjun(chemlab.lnnu@163.com) ; Li Jia(jli@simm.ac.cn)
英文摘要In order to find more efficient and low toxicity protein tyrosine phosphatase 1B (PTP1B) inhibitors, a series of novel N-acvlhvdrazone derivatives containing carbazole and aromatic ring/aromatic fused heterocycle 6 similar to 8 and 11 were designed and synthesized. Their structures and configurations were confirmed by IR, H-1 NMR, C-13 NMR, two-dimensional NMR spectra (including H-1-H-1 COSY and NOESY) and elemental analysis. The inhibitory activities of all the target compounds against PTP1B were evaluated. The experimental results indicated that all the target compounds had potent inhibitory activity against PTPIB, and the activities were higher than the control drug oleanolic acid except for N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-phenylaminoacethydrazide (6a), N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-(4-methylphenylamino)acethydrazide (6b), N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-(4-nitrophenylamino)acethydrazide (6g) and N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene)-2-(4-nitrophenylamino) acethydrazide (6h). Among them N,N'-[(9-butylcarbazolyl)-3,6-dimethylene]-2,2'-[di(4-nitrophenylamino)]bisacetohydrazide (11b) had the highest inhibitory activity against PTP1B with IC50 of (0.89 +/- 0.06) mu mol/L. Molecular docking was used to study the bind of the representative target compounds N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-(4-bromophenylamino)acethydrazide (6d), N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene)-2-((2-(1-naphthyloxy)methyl)benzimidazol-1-yl)-acethydrazide (7f) and llb with PTP1B enzyme, respectively.
WOS关键词MOLECULAR DOCKING ; BIOLOGICAL EVALUATION ; THIAZOLE DERIVATIVES ; ACID ; DISCOVERY ; DESIGN
资助项目Natural Science Foundation of Liaoning Province[20102126]
WOS研究方向Chemistry
语种英语
出版者SCIENCE PRESS
WOS记录号WOS:000706836100021
源URL[http://119.78.100.183/handle/2S10ELR8/298350]  
专题新药研究国家重点实验室
通讯作者Li Yingjun; Li Jia
作者单位1.Liaoning Normal Univ, Coll Chem & Chem Engn, Dalian 116029, Liaoning, Peoples R China
2.Dalian Univ Technol, Chem Anal & Inspect Ctr, Dalian 116023, Liaoning, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Natl Ctr Drug Screening, Shanghai 201203, Peoples R China
4.Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Liaoning, Peoples R China
推荐引用方式
GB/T 7714		 Li Yingjun,Lin Ledi,Liu Jihong,et al. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2021,41(9):3593-3607.
APA Li Yingjun.,Lin Ledi.,Liu Jihong.,Gao Lixin.,Sheng Li.,...&Li Jia.(2021).Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle.CHINESE JOURNAL OF ORGANIC CHEMISTRY,41(9),3593-3607.
MLA Li Yingjun,et al."Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle".CHINESE JOURNAL OF ORGANIC CHEMISTRY 41.9(2021):3593-3607.

入库方式： OAI收割

来源：上海药物研究所

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