Oxazolidine-2-thiones: a molecular modeling study

被引：22

作者：

Gandhi, N ^{[1
]}

Srivastava, BK ^{[1
]}

Lohray, VB ^{[1
]}

Lohray, BB ^{[1
]}

机构：

[1] Cadila Healthcare Ltd, Zydus Res Ctr, Dept Chem, Ahmedabad 382210, Gujarat, India

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 33期

关键词：

oxazolidine-2-thiones; linezolid; molecular modeling; 23S rRNA; antibacterial; piecewise linear potential (PLP); thioacetamide;

D O I：

10.1016/j.tetlet.2004.06.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two oxazolidine-2-thiones, thio-analogs of linezolid, were synthesized and their antibacterial properties evaluated. Unlike oxazolidinones, the thio-analogs did not inhibit the growth of Gram positive bacteria. A molecular modeling study has been carried out to aid understanding of this unexpected finding. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6269 / 6272

页数：4

共 19 条

[1] Prediction of binding constants of protein ligands: A fast method for the prioritization of hits obtained from de novo design or 3D database search programs [J].

Bohm, HJ .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 1998, 12 (04) :309-323

[2] THE DEVELOPMENT OF A SIMPLE EMPIRICAL SCORING FUNCTION TO ESTIMATE THE BINDING CONSTANT FOR A PROTEIN LIGAND COMPLEX OF KNOWN 3-DIMENSIONAL STRUCTURE [J].

BOHM, HJ .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 1994, 8 (03) :243-256

[3]

Brickner SJ, 1996, CURR PHARM DESIGN, V2, P175

[4] Cross-linking in the living cell locates the site of action of oxazolidinone antibiotics [J].

Colca, JR ;

McDonald, WG ;

Waldon, DJ ;

Thomasco, LM ;

Gadwood, RC ;

Lund, ET ;

Cavey, GS ;

Mathews, WR ;

Adams, LD ;

Cecil, ET ;

Pearson, JD ;

Bock, JH ;

Mott, JE ;

Shinabarger, DL ;

Xiong, LQ ;

Mankin, AS .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (24) :21972-21979

[5]

Gehlhaar D.K., 1999, ACS SYM SER, V719, P292, DOI DOI 10.1021/BK-1999-0719.CH019

[6] MOLECULAR RECOGNITION OF THE INHIBITOR AG-1343 BY HIV-1 PROTEASE - CONFORMATIONALLY FLEXIBLE DOCKING BY EVOLUTIONARY PROGRAMMING [J].

GEHLHAAR, DK ;

VERKHIVKER, GM ;

REJTO, PA ;

SHERMAN, CJ ;

FOGEL, DB ;

FOGEL, LJ ;

FREER, ST .

CHEMISTRY & BIOLOGY, 1995, 2 (05) :317-324

[7] Infections due to vancomycin-resistant Enterococcus faecium resistant to linezolid [J].

Gonzales, RD ;

Schreckenberger, PC ;

Graham, MB ;

Kelkar, S ;

DenBesten, K ;

Quinn, JP .

LANCET, 2001, 357 (9263) :1179-1179

[8]

HIROYUKI A, 2002, ANTIMICROB AGENTS CH, V46, P1080

[9] Oxazolidinone antibacterial agents: A critical review [J].

Hutchinson, DK .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2003, 3 (09) :1021-1042

[10] The oxazolidinone eperezolid binds to the 50S ribosomal subunit and competes with binding of chloramphenicol and lincomycin [J].

Lin, AH ;

Murray, RW ;

Vidmar, TJ ;

Marotti, KR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (10) :2127-2131

← 1 2 →