Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Arylaminoacetylhydrazone Derivatives Containing Carbazole Moiety

In order to find novel protein tyrosine phosphatase 1B (PTP1B) inhibitors, a series of novel arylaminoacetylhydrazone derivatives containing carbazole moiety 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, H-1-C-13 HMBC and NOESY) and elemental analysis. The inhibitory activities of all the target compounds against PTP1B were tested, and it was found that the target compounds had potent inhibitory activity against PTP1B, and most of them had lower IC50 value than the positive control drug oleanolic acid. Among them, N'-(9-octylcarbazol-3-ylmethylene)-2-(4-nitrophenylamino)acetohydrazide (3t) had the highest inhibitory activity against PTP1B with IC50 of (2.78 +/- 0.04) mu mol/L. Molecular docking was used to study the bind of compound 3t with PTP1B enzyme.

Automated summary

A series of novel arylaminoacetylhydrazone derivatives containing carbazole moiety were designed and synthesized for their potent inhibitory activity against PTP1B, with compound 3t showing the highest activity. Molecular docking was used to study the binding of compound 3t with PTP1B enzyme.