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

^*此作品的通讯作者

化学与分子工程学院

CAS - Shanghai Institute of Materia Medica
East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

63 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	6618-6622
页数	5
期刊	Bioorganic and Medicinal Chemistry Letters
卷	19
期	23
DOI	https://doi.org/10.1016/j.bmcl.2009.10.017
出版状态	已出版 - 1 12月 2009

联合国可持续发展目标

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10.1016/j.bmcl.2009.10.017

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@article{0167f5984a3a41938707601498e45666,

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",

month = dec,

day = "1",

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

language = "英语",

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pages = "6618--6622",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

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

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