Synthesis and Cdc25B/PTP1B Inhibitory Activity Evaluation of Novel Acylhydrazone Derivatives Containing Carbazole Moity

doi:10.6023/cjoc201806042

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 491-499.DOI: 10.6023/cjoc201806042 Previous Articles Next Articles

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新型含咔唑环酰腙衍生物的合成及Cdc25B/PTP1B抑制活性评价

李英俊^a, 王思远^a, 靳焜^b, 高立信^c, 盛丽^c, 张楠^a, 刘季红^d, 李佳^c

a 辽宁师范大学化学化工学院大连 116029;
b 大连理工大学精细化工国家重点实验室大连 116012;
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 大连理工大学化环生学部分析测试中心大连 116023

收稿日期:2018-06-27 修回日期:2018-08-22 发布日期:2018-09-10
通讯作者: 李佳 E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金（No.20102126）资助项目.

Synthesis and Cdc25B/PTP1B Inhibitory Activity Evaluation of Novel Acylhydrazone Derivatives Containing Carbazole Moity

Li Yingjun^a, Wang Siyuan^a, Jin Kun^b, Gao Lixin^c, Sheng Li^c, Zhang Nan^a, Liu Jihong^d, Li Jia^c

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

Received:2018-06-27 Revised:2018-08-22 Published:2018-09-10
Contact: 10.6023/cjoc201806042 E-mail:chemlab.lnnu@163.com
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

1. Synthesis and Cdc25B/PTP1B Inhibitory Activity Evaluation of Novel Acylhydrazone Derivatives Containing Carbazole Moity.PDF(1533KB)

Abstract

A series of novel acylhydrazone derivatives 6 containing carbazole moity were synthesized by carbazole and 4-cyanobenzyl chloride as starting materials via multi-step reactions. Their structures were characterized by IR, ¹H NMR, ¹³C NMR spectra and elemental analysis. All synthesized target compounds were evaluated for the inhibitory activities against Cdc25B and PTP1B. The results show that the target compounds display significant inhibitory activities against Cdc25B/PTP1B. Among them, compound 4-((carbazol-9-yl)methyl)-N'-(2-hydroxy-1-naphthalenylmethylene)benzoyl hydrazide (6g) had the highest inhibitory activities against Cdc25B and PTP1B with IC₅₀ values of (2.16±0.38) and (1.06±0.23) μg/mL, respectively. The molecular docking results indicated that the hydrogen bond and hydrophobic interaction formed between compound 6g and Cdc25B/PTP1B enzyme.

Key words: acylhydrazone, carbazole, synthesis, Cdc25B and PTP1B inhibitor, molecular docking

Cite this article

Li Yingjun, Wang Siyuan, Jin Kun, Gao Lixin, Sheng Li, Zhang Nan, Liu Jihong, Li Jia. Synthesis and Cdc25B/PTP1B Inhibitory Activity Evaluation of Novel Acylhydrazone Derivatives Containing Carbazole Moity[J]. Chin. J. Org. Chem., 2019, 39(2): 491-499.

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新型含咔唑环酰腙衍生物的合成及Cdc25B/PTP1B抑制活性评价

Synthesis and Cdc25B/PTP1B Inhibitory Activity Evaluation of Novel Acylhydrazone Derivatives Containing Carbazole Moity

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