Antibacterial activities of Groebke-Blackburn-Bienayme-derived imidazo[1,2-a]pyridin-3-amines

被引：123

作者：

Shukla, Nikunj M. ^{[1
]}

Salunke, Deepak B. ^{[1
]}

Yoo, Euna ^{[1
]}

Mutz, Cole A. ^{[1
]}

Balakrishna, Rajalakshmi ^{[1
]}

David, Sunil A. ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66047 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2012年 / 20卷 / 19期

关键词：

Antibacterials; Imidazopyridines; Antibiotics; MRSA; Bacteriostatic; Multicomponent reaction; Groebke reaction; PERMEABILITY; TOLL-LIKE-RECEPTOR-7; DERIVATIVES; PYRAZINES; AGENTS;

D O I：

10.1016/j.bmc.2012.07.052

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We sought to explore the imidazo[1,2-a]pyridin-3-amines for TLR7 (or 8)-modulatory activities. This chemotype, readily accessed via the Groebke-Blackburn-Bienayme multi-component reaction, resulted in compounds that were TLR7/8-inactive, but exhibited bacteriostatic activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). To investigate the mechanism of antibacterial activity of this new chemotype, a resistant strain of S. aureus was generated by serially passaging the organism in escalating doses of the most active analogue. A comparison of minimum inhibitory concentrations (MICs) of known bacteriostatic agents in wild-type and resistant strains indicates a novel mechanism of action. Structure-activity relationship studies have led to the identification of positions on the scaffold for additional structural modifications that should allow for the introduction of probes designed to examine cognate binding partners and molecular targets, while not significantly compromising antibacterial potency. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5850 / 5863

页数：14

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