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

Research output: Contribution to journal › Article › peer-review

60 Scopus citations

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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SDG 3 Good Health and Well-being

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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.",

author = "Jagadeshwar Vannada and Bennett, \{Eric M.\} and Wilson, \{Daniel J.\} and Boshoff, \{Helena I.\} and Barry, \{Clifton E.\} and Aldrich, \{Courtney C.\}",

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doi = "10.1021/ol0617289",

language = "English (US)",

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T1 - Design, synthesis, and biological evaluation of β-ketosulfonamide adenylation inhibitors as potential antitubercular agents

AU - Vannada, Jagadeshwar

AU - Bennett, Eric M.

AU - Wilson, Daniel J.

AU - Boshoff, Helena I.

AU - Barry, Clifton E.

AU - Aldrich, Courtney C.

PY - 2006/10/12

Y1 - 2006/10/12

N2 - (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.

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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UR - https://www.scopus.com/pages/publications/33750378701#tab=citedBy

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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

Abstract

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