Synthesis and evaluation of galactofuranosyl N,N-dialkyl sulfenamides and sulfonamides as antimycobacterial agents

被引：42

作者：

Owen, David J. ^{[1
]}

Davis, Chris B. ^{[1
]}

Hartnell, Regan D. ^{[1
]}

Madge, Paul D. ^{[1
]}

Thomson, Robin J. ^{[1
]}

Chong, Andrew K. J. ^{[1
]}

Coppel, Ross L. ^{[1
]}

von Itzstein, Mark ^{[1
]}

机构：

[1] Monash Univ, Dept Microbiol, Clayton, Vic 3168, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 08期

基金：

英国医学研究理事会; 澳大利亚研究理事会;

关键词：

galactofuranosyl; sulfenamide; sulfonamide; mycobacterium; antibacterial; inhibition;

D O I：

10.1016/j.bmcl.2007.01.068

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The recent emergence of clinically oppressive superbugs, some with resistance to nearly all frontline drug therapies, has challenged our ability to combat such infectious organisms as Mycobacterium tuberculosis, the causative agent of tuberculosis (TB). Our medicinal chemistry program targeting this pathogen has identified several potent galactofuranose-based in vitro inhibitors of mycobacterial growth. The most potent compound, the Galf N,N-didecyl sulfenamide 8d, displayed anti-mycobacterial activity (MIC) of 1 mu g/mL in a cell based assay against a representative strain of Mycobacterium smegmatis. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2274 / 2277

页数：4

共 26 条

[21] A one-pot synthesis of novel N,N-dialkyl-S-glycosylsulfenamides [J].

Owen, DJ ;

von Itzstein, M .

CARBOHYDRATE RESEARCH, 2000, 328 (03) :287-292

[22] Studies on n-octyl-5-(α-D-arabinofuranosyl)-β-D-galactofuranosides for mycobacterial glycosyltransferase activity [J].

Pathak, AK ;

Pathak, V ;

Suling, WJ ;

Gurcha, SS ;

Morehouse, CB ;

Besra, GS ;

Maddry, JA ;

Reynolds, RC .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) :923-928

[23] MICROBIAL SYSTEMS FOR STUDY OF BIOTRANSFORMATIONS OF DRUGS [J].

SMITH, RV ;

ROSAZZA, JP .

BIOTECHNOLOGY AND BIOENGINEERING, 1975, 17 (06) :785-814

[24]

VONITZSTEIN LM, 2003, Patent No. 2003070715

[25]

VONITZSTEIN LM, 2005, Patent No. 2005019237

[26] Biosynthetic origin of mycobacterial cell wall galactofuranosyl residues [J].

Weston, A ;

Stern, RJ ;

Lee, RE ;

Nassau, PM ;

Monsey, D ;

Martin, SL ;

Scherman, MS ;

Besra, GS ;

Duncan, K ;

McNeil, MR .

TUBERCLE AND LUNG DISEASE, 1998, 78 (02) :123-131

← 1 2 3 →