Literature DB >> 10450969

The synthesis and evaluation of 6-alkylidene-2'beta-substituted penam sulfones as beta-lactamase inhibitors.

J D Buynak1, A S Rao, V R Doppalapudi, G Adam, P J Petersen, S D Nidamarthy.   

Abstract

Penicillin sulfones, which structurally incorporate both a 6-position alkylidene substituent and a 2'beta substituent, have been synthesized and evaluated as inhibitors of class C and class A serine beta-lactamases. Incorporation of the 2'beta-substituent generally improves inhibitory activity. Substituents that improve transport across the bacterial cell membrane have also been incorporated.

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Year:  1999        PMID： 10450969     DOI： 10.1016/s0960-894x(99)00325-x

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


  17 in total

1.  Activity of the β-Lactamase Inhibitor LN-1-255 against Carbapenem-Hydrolyzing Class D β-Lactamases from Acinetobacter baumannii.

Authors:  Juan Carlos Vázquez-Ucha; María Maneiro; Marta Martínez-Guitián; John Buynak; Christopher R Bethel; Robert A Bonomo; Germán Bou; Margarita Poza; Concepción González-Bello; Alejandro Beceiro
Journal:  Antimicrob Agents Chemother       Date:  2017-10-24       Impact factor: 5.191

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.  Carboxylation and decarboxylation of active site Lys 84 controls the activity of OXA-24 β-lactamase of Acinetobacter baumannii: Raman crystallographic and solution evidence.

Authors:  Tao Che; Robert A Bonomo; Sivaprakash Shanmugam; Christopher R Bethel; Marianne Pusztai-Carey; John D Buynak; Paul R Carey
Journal:  J Am Chem Soc       Date:  2012-06-28       Impact factor: 15.419

4.  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

5.  β-Lactamase inhibition by 7-alkylidenecephalosporin sulfones: allylic transposition and formation of an unprecedented stabilized acyl-enzyme.

Authors:  Elizabeth A Rodkey; David C McLeod; Christopher R Bethel; Kerri M Smith; Yan Xu; Weirui Chai; Tao Che; Paul R Carey; Robert A Bonomo; Focco van den Akker; John D Buynak
Journal:  J Am Chem Soc       Date:  2013-12-03       Impact factor: 15.419

6.  Strategic design of an effective beta-lactamase inhibitor: LN-1-255, a 6-alkylidene-2'-substituted penicillin sulfone.

Authors:  Priyaranjan Pattanaik; Christopher R Bethel; Andrea M Hujer; Kristine M Hujer; Anne M Distler; Magdalena Taracila; Vernon E Anderson; Thomas R Fritsche; Ronald N Jones; Sundar Ram Reddy Pagadala; Focco van den Akker; John D Buynak; Robert A Bonomo
Journal:  J Biol Chem       Date:  2008-10-27       Impact factor: 5.157

7.  Penicillin sulfone inhibitors of class D beta-lactamases.

Authors:  Sarah M Drawz; Christopher R Bethel; Venkata R Doppalapudi; Anjaneyulu Sheri; Sundar Ram Reddy Pagadala; Andrea M Hujer; Marion J Skalweit; Vernon E Anderson; Shu G Chen; John D Buynak; Robert A Bonomo
Journal:  Antimicrob Agents Chemother       Date:  2010-01-19       Impact factor: 5.191

8.  LN-1-255, a penicillanic acid sulfone able to inhibit the class D carbapenemase OXA-48.

Authors:  Juan A Vallejo; Marta Martínez-Guitián; Juan C Vázquez-Ucha; Concepción González-Bello; Margarita Poza; John D Buynak; Christopher R Bethel; Robert A Bonomo; German Bou; Alejandro Beceiro
Journal:  J Antimicrob Chemother       Date:  2016-04-28       Impact factor: 5.790

Review 9.  Three decades of beta-lactamase inhibitors.

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

10.  Structural basis of the inhibition of class A beta-lactamases and penicillin-binding proteins by 6-beta-iodopenicillanate.

Authors:  Eric Sauvage; Astrid Zervosen; Georges Dive; Raphael Herman; Ana Amoroso; Bernard Joris; Eveline Fonzé; Rex F Pratt; André Luxen; Paulette Charlier; Frédéric Kerff
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419
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