Design, synthesis, and evaluation of novel ethambutol analogues

被引：55

作者：

Yendapally, Raghunandan ^{[1
]}

Lee, Richard E. ^{[1
]}

机构：

[1] Univ Tennessee, Ctr Hlth Sci, Dept Pharmaceut Sci, Memphis, TN 38163 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2008年 / 18卷 / 05期

关键词：

tuberculosis; anti-tuberculosis; antibiotic; ASYMMETRIC-SYNTHESIS; ARABINOFURANOSYLTRANSFERASE; IDENTIFICATION;

D O I：

10.1016/j.bmcl.2008.01.065

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Ethambutol is one of the front-line agents recommended by the World Health Organization for the treatment of tuberculosis. In an effort to develop more potent therapies to treat tuberculosis, novel unsymmetrical ethambutol analogues were successfully synthesized by a new route utilizing novel building blocks synthesized using Ellman's sulfinyl chemistry. The resulting analogues were tested for anti-tuberculosis activity yielding compounds with comparable anti-tuberculosis activity to ethambutol and increased lipophilicity that may instill better tissue penetration and serum half-life. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1607 / 1611

页数：5

共 18 条

[1] Identification of a novel arabinofuranosyltransferase (AftA) involved in cell wall Arabinan biosynthesis in Mycobacterium tuberculosis [J].

Alderwick, Luke J. ;

Seidel, Mathias ;

Sahm, Hermann ;

Besra, Gurdyal S. ;

Eggeling, Lothar .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (23) :15653-15661

[2]

BERTHELOT P, 1983, FARMACO-ED SCI, V38, P73

[3] The transcriptional responses of Mycobacterium tuberculosis to inhibitors of metabolism -: Novel insights into drug mechanisms of action [J].

Boshoff, HIM ;

Myers, TG ;

Copp, BR ;

McNeil, MR ;

Wilson, MA ;

Barry, CE .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (38) :40174-40184

[4]

Brickmann K, 1999, CHEM-EUR J, V5, P2241

[5] ANTIMYCOBACTERIAL EFFECTS OF SOME ANALOGS OF ETHAMBUTOL [J].

CREMIEUX, A ;

BAGHDADI, N ;

BERTHELOT, P ;

DEBAERT, M .

ANNALES DE MICROBIOLOGIE, 1983, A134 (02) :177-182

[6] Ethambutol analogues as potential antimycobacterial agents [J].

Häusler, H ;

Kawakami, RP ;

Mlaker, E ;

Severn, WB ;

Stütz, AE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1679-1681

[7] Discovery of aminothiazole inhibitors of cyclin-dependent kinase 2: Synthesis, X-ray crystallographic analysis, and biological activities [J].

Kim, KS ;

Kimball, SD ;

Misra, RN ;

Rawlins, DB ;

Hunt, JT ;

Xiao, HY ;

Lu, SF ;

Qian, LG ;

Han, WC ;

Shan, WF ;

Mitt, T ;

Cai, ZW ;

Poss, MA ;

Zhu, H ;

Sack, JS ;

Tokarski, JS ;

Chang, CY ;

Pavletich, N ;

Kamath, A ;

Humphreys, WG ;

Marathe, P ;

Bursuker, I ;

Kellar, KA ;

Roongta, U ;

Batorsky, R ;

Mulheron, JG ;

Bol, D ;

Fairchild, CR ;

Lee, FY ;

Webster, KR .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (18) :3905-3927

[8] Combinatorial lead optimization of [1,2]-diamines based on ethambutol as potential antituberculosis preclinical candidates [J].

Lee, RE ;

Protopopova, M ;

Crooks, E ;

Slayden, RA ;

Terrot, M ;

Barry, CE .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (02) :172-187

[9] SYNTHESIS OF THE MYCOBACTERIAL ARABINOSE DONOR BETA-D-ARABINOFURANOSYL-1-MONOPHOSPHORYLDECAPRENOL, DEVELOPMENT OF A BASIC ARABINOSYL-TRANSFERASE ASSAY, AND IDENTIFICATION OF ETHAMBUTOL AS AN ARABINOSYL TRANSFERASE INHIBITOR [J].

LEE, RE ;

MIKUSOVA, K ;

BRENNAN, PJ ;

BESRA, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) :11829-11832

[10] Catalytic asymmetric synthesis of tert-butanesulfinamide. Application to the asymmetric synthesis of amines [J].

Liu, GC ;

Cogan, DA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) :9913-9914

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