Synthesis of 4-Phenyl-1,3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B

doi:10.11944/j.issn.1000-0518.2019.07.180381

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (7): 749-757.DOI: 10.11944/j.issn.1000-0518.2019.07.180381

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Synthesis of 4-Phenyl-1,3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B

ZHANG Chenglu(),WANG Huayu,LI Yilin,WANG Yiming,GONG Rongqing,SUN Yuedong,SONG Fulu

College of Chemistry and Chemical Engineering, Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2018-11-29 Accepted:2019-02-25 Published:2019-07-01 Online:2019-07-02
Contact: Chenglu ZHANG
Supported by:
Supported by the Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)

Abstract

Abstract:

Protein tyrosine phosphatase-1B(PTP1B) is an important target for anti-diabetic treatment. That means the creation of PTP1B inhibitors with excellent activity is undoubtedly of great significance. In this paper, eleven molecules with novel structures(ZLXZ1-ZLXZ11) containing 1,3-selenazole and 1,2,4-triazole active blocks were designed and synthesized. Their structures were characterized by Fourier transform infrared spectrometer(FTIR), nuclear magnetic resonance spectroscopy(NMR) and high resolution mass spectrometry(HRMS). First, ZLXZ1 and ZLXZ11 were selected for molecular docking simulation with PTP1B on MOE 2015.10. As a result, π-H action and hydrogen bonding are formed respectively between the selenium atom on the selenazole ring in ZLXZ1 and the secondary catalytic sites Tyr46 and Asp48 in PTP1B. The selenium atom on the selenazole in the ZLXZ11 molecule forms a hydrogen bond with Asp 181, which facilitates the binding of the molecule to PTP1B. On this basis, the inhibitory activities of 11 target molecules were evaluated. The results show that the inhibition rates of the target molecules are all above 87.02%, in which three target molecules are better than that of the positive control, oleanolic acid, which indicates that these novel structures are expected to be potential PTP1B inhibitors.

Key words: 1,3-selenazole, 1,2,4-triazole Schiff base, molecular docking simulation, protein tyrosine phosphatase-1B inhibitor

ZHANG Chenglu, WANG Huayu , LI Yilin, WANG Yiming, GONG Rongqing, SUN Yuedong, SONG Fulu. Synthesis of 4-Phenyl-1,3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B[J]. Chinese Journal of Applied Chemistry, 2019, 36(7): 749-757.

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Synthesis of 4-Phenyl-1,3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B

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