Structure–activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors

Qianbin Li; Adnan Al-Ayoubi; Tailiang Guo; Hui Zheng; Aurijit Sarkar; Tri Nguyen; Scott T. Eblen; Steven Grant; Glen E. Kellogg; Shijun Zhang

doi:10.1016/j.bmcl.2009.09.057

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Structure–activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors

Journal article

Peer reviewed

Structure–activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors

Qianbin Li, Adnan Al-Ayoubi, Tailiang Guo, Hui Zheng, Aurijit Sarkar, Tri Nguyen, Scott T. Eblen, Steven Grant, Glen E. Kellogg and Shijun Zhang

Bioorganic & medicinal chemistry letters, Vol.19(21), pp.6042-6046

11/01/2009

DOI: 10.1016/j.bmcl.2009.09.057

PMCID: PMC6088847

PMID: 19796943

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Abstract

Preliminary structure–activity relationship studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione, a putative substrate-specific ERK1/2 inhibitor, is reported. A series of analogs of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione, a putative substrate-specific ERK1/2 inhibitor, were synthesized and biologically characterized in human leukemia U937 cells to define its pharmacophore. It was discovered that shift of ethoxy substitution from the 4- to the 2-position on the phenyl ring significantly improved functional activities of inhibiting cell proliferation and inducing apoptosis. This may provide access to a new lead for developing ERK1/2 substrate-specific inhibitors.

ERK1/2

Molecular modeling

Rational design

SAR

Substrate-specific inhibitor

Synthesis

Thiazolidine-2,4-dione

Details

Title: Subtitle: Structure–activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors
Creators: Qianbin Li - Virginia Commonwealth University
Adnan Al-Ayoubi - Medical University of South Carolina
Tailiang Guo - Virginia Commonwealth University
Hui Zheng - Medical University of South Carolina
Aurijit Sarkar - Virginia Commonwealth University
Tri Nguyen - Virginia Commonwealth University
Scott T. Eblen - Medical University of South Carolina
Steven Grant - Virginia Commonwealth University
Glen E. Kellogg - Virginia Commonwealth University
Shijun Zhang - Virginia Commonwealth University
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry letters, Vol.19(21), pp.6042-6046
Publisher: Elsevier Ltd
DOI: 10.1016/j.bmcl.2009.09.057
PMID: 19796943
PMCID: PMC6088847
ISSN: 0960-894X
eISSN: 1464-3405
Number of pages: 5
Language: English
Date published: 11/01/2009
Academic Unit: Cardiothoracic Surgery
Record Identifier: 9984701735602771

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