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

School of Chemistry and Molecular Engineering

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

62 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

Keywords

Diabetes
Inhibitor
Maslinic acid
Protein tyrosine phosphatase 1B
SAR

UN SDGs

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

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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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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

Keywords

UN SDGs

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