Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives

doi:10.6023/cjoc201907043

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 478-488.DOI: 10.6023/cjoc201907043 Previous Articles Next Articles

基于咔唑的新型碳酰腙衍生物的合成及蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性评价

李英俊^a, 刘雪洁^a, 刘季红^b, 高立信^c, 靳焜^d, 盛丽^c, 杨鸿境^a, 林乐弟^a, 李佳^c

a 辽宁师范大学化学化工学院大连 116029;
b 大连理工大学化学分析测试中心大连 116023;
c 中国科学院上海药物研究所国家新药筛选中心药物研究国家重点实验室上海 201203;
d 大连理工大学精细化工国家重点实验室大连 116012

收稿日期:2019-07-27 修回日期:2019-09-09 发布日期:2019-10-09
通讯作者: 李英俊, 李佳 E-mail:chemlab.lnnu@163.com;jli@simm.ac.cn
基金资助:
辽宁省自然科学基金（No.20102126）资助项目.

Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives

Li Yingjun^a, Liu Xuejie^a, Liu Jihong^b, Gao Lixin^c, Jin Kun^d, Sheng Li^c, Yang Hongjing^a, Lin Ledi^a, Li Jia^c

a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
b Chemistry Analysis and Inspection Center, Dalian University of Technology, Dalian 116023;
c National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
d State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Received:2019-07-27 Revised:2019-09-09 Published:2019-10-09
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

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Abstract

A series of novel carbazole-based mono-/bis-carbohydrazone derivatives 3 and 4 were synthesized. Their structures were characterized by ¹H NMR, ¹³C NMR, IR spectra and elemental analysis. The inhibitory activities of all synthesized compounds against protein tyrosine phosphatase 1B (PTP1B) were evaluated, and the structure-activity relationship was discussed. The results indicated that most of the compounds had good inhibitory activity against PTP1B, and 1,5-bis[(9-butyl-3-carba-zolyl)methylene]carbohydrazone (4c) showed the highest inhibitory activity against PTP1B with IC₅₀=(4.81±0.41) μmol/L and the activity was higher than that of the control drug oleanolic acid. Molecular docking and density functional theory (DFT) calculations of 3f and 4c were carried out. The results of molecular docking indicated that 1-[(9-heptyl-3-carbazolyl)meth-ylene]carbohydrazone (3f) and 4c bind to an active site of PTP1B enzyme formed by the helices α3 and α6, and formed a stable complex respectively with PTP1B enzyme by hydrogen bonds, polar, hydrophobic and π-π interactions.

Key words: carbohydrazone, carbazole, synthesis, PTP1B inhibitor, molecular docking, DFT calculations

Cite this article

Li Yingjun, Liu Xuejie, Liu Jihong, Gao Lixin, Jin Kun, Sheng Li, Yang Hongjing, Lin Ledi, Li Jia. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 478-488.

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基于咔唑的新型碳酰腙衍生物的合成及蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性评价

Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives

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