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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 2: 478 - 488

DOI: https://doi.org/10.6023/cjoc201907043

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

  • Li Yingjun ,
  • Liu Xuejie ,
  • Liu Jihong ,
  • Gao Lixin ,
  • Jin Kun ,
  • Sheng Li ,
  • Yang Hongjing ,
  • Lin Ledi ,
  • Li Jia
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  • 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 date: 2019-07-27

  Revised date: 2019-09-09

  Online 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 . DOI: 10.6023/cjoc201907043

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