Literature DB >> 17020283

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

Jagadeshwar Vannada1, Eric M Bennett, Daniel J Wilson, Helena I Boshoff, Clifton E Barry, Courtney C Aldrich.   

Abstract

[reaction: see text] 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 beta-ketosulfonamide linkage of 3 and 4.

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Year:  2006        PMID： 17020283      PMCID： PMC2596716          DOI： 10.1021/ol0617289

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

Review 1.  Genetics and assembly line enzymology of siderophore biosynthesis in bacteria.

Authors:  Jorge H Crosa; Christopher T Walsh
Journal:  Microbiol Mol Biol Rev       Date:  2002-06       Impact factor: 11.056

2.  Rationally designed nucleoside antibiotics that inhibit siderophore biosynthesis of Mycobacterium tuberculosis.

Authors:  Ravindranadh V Somu; Helena Boshoff; Chunhua Qiao; Eric M Bennett; Clifton E Barry; Courtney C Aldrich
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

3.  A genetic locus required for iron acquisition in Mycobacterium tuberculosis.

Authors:  R Krithika; Uttara Marathe; Priti Saxena; Mohd Zeeshan Ansari; Debasisa Mohanty; Rajesh S Gokhale
Journal:  Proc Natl Acad Sci U S A       Date:  2006-02-03       Impact factor: 11.205

Review 4.  Mycobactins: iron-chelating growth factors from mycobacteria.

Authors:  G A Snow
Journal:  Bacteriol Rev       Date:  1970-06

5.  Elemental analysis of Mycobacterium avium-, Mycobacterium tuberculosis-, and Mycobacterium smegmatis-containing phagosomes indicates pathogen-induced microenvironments within the host cell's endosomal system.

Authors:  Dirk Wagner; Jörg Maser; Barry Lai; Zhonghou Cai; Clifton E Barry; Kerstin Höner Zu Bentrup; David G Russell; Luiz E Bermudez
Journal:  J Immunol       Date:  2005-02-01       Impact factor: 5.422

6.  Mycobactin-mediated iron acquisition within macrophages.

Authors:  Minkui Luo; Evgeny A Fadeev; John T Groves
Journal:  Nat Chem Biol       Date:  2005-07-03       Impact factor: 15.040

7.  Second generation fluorous DEAD reagents have expanded scope in the Mitsunobu reaction and retain convenient separation features.

Authors:  Sivaraman Dandapani; Dennis P Curran
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

8.  Identification of a Mycobacterium tuberculosis gene cluster encoding the biosynthetic enzymes for assembly of the virulence-conferring siderophore mycobactin.

Authors:  L E Quadri; J Sello; T A Keating; P H Weinreb; C T Walsh
Journal:  Chem Biol       Date:  1998-11

9.  Cerium(III) chloride-mediated reactions of sulfonamide dianions.

Authors:  David C Johnson; Theodore S Widlanski
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354

10.  The design and synthesis of sulfonamides as caspase-1 inhibitors.

Authors:  William G Harter; Hans Albrect; Kenneth Brady; Bradley Caprathe; James Dunbar; John Gilmore; Sheryl Hays; Catherine R Kostlan; Beth Lunney; Nigel Walker
Journal:  Bioorg Med Chem Lett       Date:  2004-02-09       Impact factor: 2.823
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  29 in total

1.  Structure-activity relationship of new anti-tuberculosis agents derived from oxazoline and oxazole benzyl esters.

Authors:  Garrett C Moraski; Mayland Chang; Adriel Villegas-Estrada; Scott G Franzblau; Ute Möllmann; Marvin J Miller
Journal:  Eur J Med Chem       Date:  2010-01-14       Impact factor: 6.514

Review 2.  Adenylating enzymes in Mycobacterium tuberculosis as drug targets.

Authors:  Benjamin P Duckworth; Kathryn M Nelson; Courtney C Aldrich
Journal:  Curr Top Med Chem       Date:  2012       Impact factor: 3.295

3.  Antitubercular nucleosides that inhibit siderophore biosynthesis: SAR of the glycosyl domain.

Authors:  Ravindranadh V Somu; Daniel J Wilson; Eric M Bennett; Helena I Boshoff; Laura Celia; Brian J Beck; Clifton E Barry; Courtney C Aldrich
Journal:  J Med Chem       Date:  2006-12-28       Impact factor: 7.446

4.  A mechanism-based aryl carrier protein/thiolation domain affinity probe.

Authors:  Chunhua Qiao; Daniel J Wilson; Eric M Bennett; Courtney C Aldrich
Journal:  J Am Chem Soc       Date:  2007-05-01       Impact factor: 15.419

5.  Inhibition of siderophore biosynthesis by 2-triazole substituted analogues of 5'-O-[N-(salicyl)sulfamoyl]adenosine: antibacterial nucleosides effective against Mycobacterium tuberculosis.

Authors:  Amol Gupte; Helena I Boshoff; Daniel J Wilson; João Neres; Nicholas P Labello; Ravindranadh V Somu; Chengguo Xing; Clifton E Barry; Courtney C Aldrich
Journal:  J Med Chem       Date:  2008-12-11       Impact factor: 7.446

6.  Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: structure-activity relationships of the nucleobase domain of 5'-O-[N-(salicyl)sulfamoyl]adenosine.

Authors:  João Neres; Nicholas P Labello; Ravindranadh V Somu; Helena I Boshoff; Daniel J Wilson; Jagadeshwar Vannada; Liqiang Chen; Clifton E Barry; Eric M Bennett; Courtney C Aldrich
Journal:  J Med Chem       Date:  2008-08-09       Impact factor: 7.446

7.  Synthesis of chromone, quinolone, and benzoxazinone sulfonamide nucleosides as conformationally constrained inhibitors of adenylating enzymes required for siderophore biosynthesis.

Authors:  Curtis A Engelhart; Courtney C Aldrich
Journal:  J Org Chem       Date:  2013-07-12       Impact factor: 4.354

Review 8.  Small molecule inhibition of microbial natural product biosynthesis-an emerging antibiotic strategy.

Authors:  Justin S Cisar; Derek S Tan
Journal:  Chem Soc Rev       Date:  2008-05-21       Impact factor: 54.564

Review 9.  Siderophore-based iron acquisition and pathogen control.

Authors:  Marcus Miethke; Mohamed A Marahiel
Journal:  Microbiol Mol Biol Rev       Date:  2007-09       Impact factor: 11.056

10.  Quantitative three dimensional structure linear interaction energy model of 5'-O-[N-(salicyl)sulfamoyl]adenosine and the aryl acid adenylating enzyme MbtA.

Authors:  Nicholas P Labello; Eric M Bennett; David M Ferguson; Courtney C Aldrich
Journal:  J Med Chem       Date:  2008-11-27       Impact factor: 7.446
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