Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

Wen Wei Qiu; Qiang Shen; Fan Yang; Bo Wang; Hui Zou; Jing Ya Li; Jia Li; Jie Tang

doi:10.1016/j.bmcl.2009.10.017

Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

Wen Wei Qiu
, Qiang Shen
, Fan Yang
, Bo Wang
, Hui Zou
, Jing Ya Li
, Jia Li^*
, Jie Tang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

CAS - Shanghai Institute of Materia Medica
East China Normal University

Research output: Contribution to journal › Article › peer-review

63 Scopus citations

Abstract

A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC₅₀ = 0.61 μM) and 29 (IC₅₀ = 0.64 μM) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP.

Original language	English
Pages (from-to)	6618-6622
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2009.10.017
State	Published - 1 Dec 2009

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Diabetes
Inhibitor
Maslinic acid
Protein tyrosine phosphatase 1B
SAR

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10.1016/j.bmcl.2009.10.017

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title = "Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B",

abstract = "A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 μM) and 29 (IC50 = 0.64 μM) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP.",

keywords = "Diabetes, Inhibitor, Maslinic acid, Protein tyrosine phosphatase 1B, SAR",

author = "Qiu, \{Wen Wei\} and Qiang Shen and Fan Yang and Bo Wang and Hui Zou and Li, \{Jing Ya\} and Jia Li and Jie Tang",

year = "2009",

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doi = "10.1016/j.bmcl.2009.10.017",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

AU - Qiu, Wen Wei

AU - Shen, Qiang

AU - Yang, Fan

AU - Wang, Bo

AU - Zou, Hui

AU - Li, Jing Ya

AU - Li, Jia

AU - Tang, Jie

PY - 2009/12/1

Y1 - 2009/12/1

N2 - A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 μM) and 29 (IC50 = 0.64 μM) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP.

AB - A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 μM) and 29 (IC50 = 0.64 μM) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP.

KW - Diabetes

KW - Inhibitor

KW - Maslinic acid

KW - Protein tyrosine phosphatase 1B

KW - SAR

UR - https://www.scopus.com/pages/publications/71749095585

U2 - 10.1016/j.bmcl.2009.10.017

DO - 10.1016/j.bmcl.2009.10.017

M3 - 文章

C2 - 19846303

AN - SCOPUS:71749095585

SN - 0960-894X

VL - 19

SP - 6618

EP - 6622

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

Abstract

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Keywords

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