Design, synthesis, and biological evaluation of β-ketosulfonamide adenylation inhibitors as potential antitubercular agents

Jagadeshwar Vannada; Eric M. Bennett; Daniel J. Wilson; Helena I. Boshoff; Clifton E. Barry; Courtney C. Aldrich

doi:10.1021/ol0617289

Design, synthesis, and biological evaluation of β-ketosulfonamide adenylation inhibitors as potential antitubercular agents

Jagadeshwar Vannada, Eric M. Bennett, Daniel J. Wilson, Helena I. Boshoff, Clifton E. Barry, Courtney C. Aldrich

Medicinal Chemistry

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Abstract

(Chemical Equation Presented) The antitubercular nucleoside antibiotics 1 and 2 were recently described that inhibit the adenylate-forming enzyme MbtA and disrupt biosynthesis of the virulence-conferring siderophore known as mycobactin in Mycobacterium tuberculosis. Herein, we report efforts to refine this inhibitor scaffold by replacing the labile acylsulfamate linkage (highlighted) with the more chemically robust β-ketosulfonamide linkage of 3 and 4.

Original language	English (US)
Pages (from-to)	4707-4710
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	21
DOIs	https://doi.org/10.1021/ol0617289
State	Published - Oct 12 2006

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title = "Design, synthesis, and biological evaluation of β-ketosulfonamide adenylation inhibitors as potential antitubercular agents",

abstract = "(Chemical Equation Presented) The antitubercular nucleoside antibiotics 1 and 2 were recently described that inhibit the adenylate-forming enzyme MbtA and disrupt biosynthesis of the virulence-conferring siderophore known as mycobactin in Mycobacterium tuberculosis. Herein, we report efforts to refine this inhibitor scaffold by replacing the labile acylsulfamate linkage (highlighted) with the more chemically robust β-ketosulfonamide linkage of 3 and 4.",

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AU - Boshoff, Helena I.

AU - Barry, Clifton E.

AU - Aldrich, Courtney C.

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AB - (Chemical Equation Presented) The antitubercular nucleoside antibiotics 1 and 2 were recently described that inhibit the adenylate-forming enzyme MbtA and disrupt biosynthesis of the virulence-conferring siderophore known as mycobactin in Mycobacterium tuberculosis. Herein, we report efforts to refine this inhibitor scaffold by replacing the labile acylsulfamate linkage (highlighted) with the more chemically robust β-ketosulfonamide linkage of 3 and 4.

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Design, synthesis, and biological evaluation of β-ketosulfonamide adenylation inhibitors as potential antitubercular agents

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