Inhibition of Siderophore Biosynthesis by 2-Triazole Substituted Analogues of 5'-O-N-(Salicyl)sulfamoyladenosine: Antibacterial Nucleosides Effective against Mycobacterium tuberculosis

Gupte  A; Boshoff  HI; Wilson  DJNeres  JLabello  NPSomu  RVXing  CGBarry  CEAldrich  CC

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Inhibition of Siderophore Biosynthesis by 2-Triazole Substituted Analogues of 5'-O-N-(Salicyl)sulfamoyladenosine: Antibacterial Nucleosides Effective against Mycobacterium tuberculosis

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The synthesis, biochemical, and biological evaluation of a systematic series of 2-triazole derivatives of 5'-O-N-(salicyl)sulfamoyladenosine (Sal-AMS) are described as inhibitors of aryl acid adenylating enzymes (AAAE) involved in siderophore biosynthesis by Mycobacterium tuberculosis. Structure-activity relationships revealed a remarkable ability to tolerate a wide range of substituents at the 4-position of the triazole moiety, and a majority of the Compounds possessed subnanomolar apparent inhibition constants. However, the in vitro potency did not always translate into whole cell biological activity against M. tuberculosis, suggesting that intrinsic resistance plays an important role in the observed activities. Additionally, the well-known valence tautomerism between 2-azidopurines and their fused tetrazole counterparts led to an unexpected facile acylation of the purine N-6 amino group.

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《Journal of Medicinal Chemistry》 |2008年第23期|7495-7507|共13页
作者
Gupte A; Boshoff HI; Wilson DJNeres JLabello NPSomu RVXing CGBarry CEAldrich CC;
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[Gupte, A;

Wilson, DJ;

Neres, JLabello, NPSomu, RVAldrich, CC] Univ Minnesota, Acad Hlth Ctr, Ctr Drug Design, Minneapolis, MN 55455 USA[Boshoff, HIBarry, CE] NIAID, TB Res Sect, Bethesda, MD 20892 USA[Xing, CG] Univ Minnesota, Dept Med Chem, Minneapolis, MN 55455 USA;

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正文语种英语
中图分类药学;
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ANTITUBERCULAR AGENTS; PEPTIDE SYNTHETASES; COUPLING REACTIONS; RECEPTOR AGONISTS; IRON ACQUISITION; TERMINAL ALKYNES; FACILE SYNTHESIS; AZIDES; ENZYME; DOMAIN;

Inhibition of Siderophore Biosynthesis by 2-Triazole Substituted Analogues of 5'-O-N-(Salicyl)sulfamoyladenosine: Antibacterial Nucleosides Effective against Mycobacterium tuberculosis

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