Literature DB >> 10230626

6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C beta-lactamases I.

P Bitha1, Z Li, G D Francisco, B A Rasmussen, Y I Lin.   

Abstract

Five 6-(1-hydroxyalkyl)penam sulfone derivatives and two 6-(hydroxymethyl)penams were synthesized for beta-lactamase inhibitor screens. The substituent effects and stereochemical requirements of 6alpha- and 6beta-(1-hydroxyalkyl) groups for the biological activity of penam sulfone derivatives were investigated. Of these substituents, only the 6beta-hydroxymethyl group of 15 improved the activity of sulbactam against both TEM-1 and AmpC beta-lactamases. The sulfone moiety is required for the enhancement of the beta-lactamase inhibitory activity. 6Beta-hydroxymethylsulbactam (15) was able to restore the activity of piperacillin in vitro and in vivo against various beta-lactamase producing microorganisms.

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Year:  1999        PMID： 10230626     DOI： 10.1016/s0960-894x(99)00106-7

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  8 in total

1.  Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy.

Authors:  Micheal Nottingham; Christopher R Bethel; Sundar Ram Reddy Pagadala; Emily Harry; Abishai Pinto; Zachary A Lemons; Sarah M Drawz; Focco van den Akker; Paul R Carey; Robert A Bonomo; John D Buynak
Journal:  Bioorg Med Chem Lett       Date:  2010-11-05       Impact factor: 2.823

Review 2.  Current challenges in antimicrobial chemotherapy: focus on ß-lactamase inhibition.

Authors:  Carine Bebrone; Patricia Lassaux; Lionel Vercheval; Jean-Sébastien Sohier; Adrien Jehaes; Eric Sauvage; Moreno Galleni
Journal:  Drugs       Date:  2010-04-16       Impact factor: 9.546

3.  Inactivation of a class A and a class C β-lactamase by 6β-(hydroxymethyl)penicillanic acid sulfone.

Authors:  Krisztina M Papp-Wallace; Christopher R Bethel; Thomas D Gootz; Wenchi Shang; Justin Stroh; William Lau; Dale McLeod; Loren Price; Anthony Marfat; Anne Distler; Sarah M Drawz; Hansong Chen; Emily Harry; Micheal Nottingham; Paul R Carey; John D Buynak; Robert A Bonomo
Journal:  Biochem Pharmacol       Date:  2011-12-02       Impact factor: 5.858

4.  Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.

Authors:  Sebastian A Testero; Peter I O'Daniel; Qicun Shi; Mijoon Lee; Dusan Hesek; Akihiro Ishiwata; Bruce C Noll; Shahriar Mobashery
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

Review 5.  Three decades of beta-lactamase inhibitors.

Authors:  Sarah M Drawz; Robert A Bonomo
Journal:  Clin Microbiol Rev       Date:  2010-01       Impact factor: 26.132

6.  Approaches to the simultaneous inactivation of metallo- and serine-beta-lactamases.

Authors:  Sudhakar Reddy Ganta; Senthil Perumal; Sundar Ram Reddy Pagadala; Orjan Samuelsen; James Spencer; R F Pratt; John D Buynak
Journal:  Bioorg Med Chem Lett       Date:  2009-02-08       Impact factor: 2.823

7.  Detecting a quasi-stable imine species on the reaction pathway of SHV-1 β-lactamase and 6β-(hydroxymethyl)penicillanic acid sulfone.

Authors:  Tao Che; Elizabeth A Rodkey; Christopher R Bethel; Sivaprakash Shanmugam; Zhe Ding; Marianne Pusztai-Carey; Michael Nottingham; Weirui Chai; John D Buynak; Robert A Bonomo; Focco van den Akker; Paul R Carey
Journal:  Biochemistry       Date:  2015-01-08       Impact factor: 3.162

Review 8.  Exploring Additional Dimensions of Complexity in Inhibitor Design for Serine β-Lactamases: Mechanistic and Intra- and Inter-molecular Chemistry Approaches.

Authors:  Focco van den Akker; Robert A Bonomo
Journal:  Front Microbiol       Date:  2018-04-05       Impact factor: 5.640
  8 in total

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