Literature DB >> 21392987

Synthesis and SAR of novel benzoxaboroles as a new class of β-lactamase inhibitors.

Yi Xia1, Kathy Cao, Yasheen Zhou, M R K Alley, Fernando Rock, Manisha Mohan, Maliwan Meewan, Stephen J Baker, Sarah Lux, Charles Z Ding, Guofeng Jia, Maureen Kully, Jacob J Plattner.   

Abstract

A new class of benzoxaborole β-lactamase inhibitors were designed and synthesized. 6-Aryloxy benzoxaborole 22 inhibited AmpC P99 and CMY-2 with K(i) values in the low nanomolar range. Compound 22 restored antibacterial activity of ceftazidime against Enterobacter cloacae P99 expressing AmpC, a class C β-lactamase enzyme. The SAR around the arylbenzoxaboroles, which included the influence of linker and substitutions was also established.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21392987     DOI： 10.1016/j.bmcl.2011.02.024

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


  22 in total

1.  Antimalarial Benzoxaboroles Target Plasmodium falciparum Leucyl-tRNA Synthetase.

Authors:  Ebere Sonoiki; Andres Palencia; Denghui Guo; Vida Ahyong; Chen Dong; Xianfeng Li; Vincent S Hernandez; Yong-Kang Zhang; Wai Choi; Jiri Gut; Jennifer Legac; Roland Cooper; M R K Alley; Yvonne R Freund; Joseph DeRisi; Stephen Cusack; Philip J Rosenthal
Journal:  Antimicrob Agents Chemother       Date:  2016-07-22       Impact factor: 5.191

2.  A Divalent Protecting Group for Benzoxaboroles.

Authors:  Brett Vanveller; Matthew R Aronoff; Ronald T Raines
Journal:  RSC Adv       Date:  2013-11-28       Impact factor: 3.361

3.  Synthesis and evaluation of functionalized benzoboroxoles as potential anti-tuberculosis agents.

Authors:  Mohammad A Alam; Kriti Arora; Shirisha Gurrapu; Sravan K Jonnalagadda; Grady L Nelson; Paul Kiprof; Subash C Jonnalagadda; Venkatram R Mereddy
Journal:  Tetrahedron       Date:  2016-03-17       Impact factor: 2.457

4.  Exploring the potential of boronic acids as inhibitors of OXA-24/40 β-lactamase.

Authors:  Josephine P Werner; Joshua M Mitchell; Magdalena A Taracila; Robert A Bonomo; Rachel A Powers
Journal:  Protein Sci       Date:  2017-02-23       Impact factor: 6.725

5.  Antibacterial Activity and Mode of Action of a Sulfonamide-Based Class of Oxaborole Leucyl-tRNA-Synthetase Inhibitors.

Authors:  Yuanyuan Si; Sneha Basak; Yong Li; Jonathan Merino; James N Iuliano; Stephen G Walker; Peter J Tonge
Journal:  ACS Infect Dis       Date:  2019-05-01       Impact factor: 5.084

6.  Modification of triclosan scaffold in search of improved inhibitors for enoyl-acyl carrier protein (ACP) reductase in Toxoplasma gondii.

Authors:  Jozef Stec; Alina Fomovska; Gustavo A Afanador; Stephen P Muench; Ying Zhou; Bo-Shiun Lai; Kamal El Bissati; Mark R Hickman; Patty J Lee; Susan E Leed; Jennifer M Auschwitz; Caroline Sommervile; Stuart Woods; Craig W Roberts; David Rice; Sean T Prigge; Rima McLeod; Alan P Kozikowski
Journal:  ChemMedChem       Date:  2013-06-14       Impact factor: 3.466

7.  Development of a triclosan scaffold which allows for adaptations on both the A- and B-ring for transport peptides.

Authors:  Stephen P Muench; Jozef Stec; Ying Zhou; Gustavo A Afanador; Martin J McPhillie; Mark R Hickman; Patty J Lee; Susan E Leed; Jennifer M Auschwitz; Sean T Prigge; David W Rice; Rima McLeod
Journal:  Bioorg Med Chem Lett       Date:  2013-04-24       Impact factor: 2.823

Review 8.  Synthesis of biologically active boron-containing compounds.

Authors:  Fei Yang; Mingyan Zhu; Jinyi Zhang; Huchen Zhou
Journal:  Medchemcomm       Date:  2017-11-28       Impact factor: 3.597

9.  Benzoxaborole antimalarial agents. Part 4. Discovery of potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles.

Authors:  Yong-Kang Zhang; Jacob J Plattner; Eric E Easom; Robert T Jacobs; Denghui Guo; Virginia Sanders; Yvonne R Freund; Brice Campo; Philip J Rosenthal; Wei Bu; Francisco-Javier Gamo; Laura M Sanz; Min Ge; Liang Li; Jie Ding; Yin Yang
Journal:  J Med Chem       Date:  2015-06-23       Impact factor: 7.446

10.  Clinical and veterinary trypanocidal benzoxaboroles target CPSF3.

Authors:  Richard J Wall; Eva Rico; Iva Lukac; Fabio Zuccotto; Sara Elg; Ian H Gilbert; Yvonne Freund; M R K Alley; Mark C Field; Susan Wyllie; David Horn
Journal:  Proc Natl Acad Sci U S A       Date:  2018-09-05       Impact factor: 11.205
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