Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 491-499. doi: 10.6023/cjoc201806042 shu

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

Corresponding author: Li Jia, chemlab.lnnu@163.com
Received Date: 27 June 2018
Revised Date: 22 August 2018
Available Online: 10 February 2018
Fund Project: Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126)the Natural Science Foundation of Liaoning Province 20102126

Figures(5)

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.
- acylhydrazone,
- carbazole,
- synthesis,
- Cdc25B and PTP1B inhibitor,
- molecular docking
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