Literature DB >> 28523106

Discovery of Fluorine-Containing Benzoxazinyl-oxazolidinones for the Treatment of Multidrug Resistant Tuberculosis.

Hongyi Zhao1,2, Yu Lu3, Li Sheng1, Zishuo Yuan1, Bin Wang3, Weiping Wang1, Yan Li1, Chen Ma1, Xiaoliang Wang1, Dongfeng Zhang1,2, Haihong Huang1,2.   

Abstract

A novel series of fluorine-containing benzoxazinyl-oxazolidinones were designed and synthesized as antidrug-resistant tuberculosis agents possessing good activity and improved pharmacokinetic profiles. Compound 21 exhibited not only outstanding in vitro activity with a MIC value of 0.25-0.50 μg/mL against drug-susceptible H37Rv strain and two clinically isolated drug-resistant Mycobacterium tuberculosis strains, but also acceptable in vitro ADME/T properties. Moreover, this compound displayed excellent mouse pharmacokinetic profiles with an oral bioavailability of 102% and a longer elimination half-life of 4.22 h, thereby supporting further optimization and development of this promising lead series.

Entities:  

Keywords:  Antitubercular agents; drug-resistant tuberculosis (DR-TB); fluoro-benzoxazinyl-oxazolidinones; structure−activity relationships

Year:  2017        PMID： 28523106      PMCID： PMC5430409          DOI： 10.1021/acsmedchemlett.7b00068

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  18 in total

1.  Design, synthesis, and structure-activity relationship studies of highly potent novel benzoxazinyl-oxazolidinone antibacterial agents.

Authors:  Qisheng Xin; Houxing Fan; Bin Guo; Huili He; Suo Gao; Hui Wang; Yanqin Huang; Yushe Yang
Journal:  J Med Chem       Date:  2011-10-12       Impact factor: 7.446

Review 2.  New trends in development of antimycobacterial compounds.

Authors:  M Biava; G C Porretta; D Deidda; R Pompei
Journal:  Infect Disord Drug Targets       Date:  2006-06

3.  Inhibition of mammalian mitochondrial protein synthesis by oxazolidinones.

Authors:  E E McKee; M Ferguson; A T Bentley; T A Marks
Journal:  Antimicrob Agents Chemother       Date:  2006-06       Impact factor: 5.191

Review 4.  Oxazolidinone antibiotics.

Authors:  D J Diekema; R N Jones
Journal:  Lancet       Date:  2001-12-08       Impact factor: 79.321

Review 5.  Tuberculosis treatment and management--an update on treatment regimens, trials, new drugs, and adjunct therapies.

Authors:  Alimuddin Zumla; Jeremiah Chakaya; Rosella Centis; Lia D'Ambrosio; Peter Mwaba; Matthew Bates; Nathan Kapata; Thomas Nyirenda; Duncan Chanda; Sayoki Mfinanga; Michael Hoelscher; Markus Maeurer; Giovanni Battista Migliori
Journal:  Lancet Respir Med       Date:  2015-03-09       Impact factor: 30.700

Review 6.  Totally drug-resistant tuberculosis and adjunct therapies.

Authors:  S K Parida; R Axelsson-Robertson; M V Rao; N Singh; I Master; A Lutckii; S Keshavjee; J Andersson; A Zumla; M Maeurer
Journal:  J Intern Med       Date:  2014-06-18       Impact factor: 8.989

7.  A retrospective TBNET assessment of linezolid safety, tolerability and efficacy in multidrug-resistant tuberculosis.

Authors:  G B Migliori; B Eker; M D Richardson; G Sotgiu; J-P Zellweger; A Skrahina; J Ortmann; E Girardi; H Hoffmann; G Besozzi; N Bevilacqua; D Kirsten; R Centis; C Lange
Journal:  Eur Respir J       Date:  2009-03-12       Impact factor: 16.671

8.  Design, synthesis, and structure-activity and structure-pharmacokinetic relationship studies of novel [6,6,5] tricyclic fused oxazolidinones leading to the discovery of a potent, selective, and orally bioavailable FXa inhibitor.

Authors:  Tao Xue; Shi Ding; Bin Guo; Yuren Zhou; Peng Sun; Heyao Wang; Wenjing Chu; Guoqing Gong; Yinye Wang; Xiaoyan Chen; Yushe Yang
Journal:  J Med Chem       Date:  2014-09-15       Impact factor: 7.446

9.  Bactericidal activity and mechanism of action of AZD5847, a novel oxazolidinone for treatment of tuberculosis.

Authors:  V Balasubramanian; S Solapure; H Iyer; A Ghosh; S Sharma; P Kaur; R Deepthi; V Subbulakshmi; V Ramya; V Ramachandran; M Balganesh; L Wright; D Melnick; S L Butler; V K Sambandamurthy
Journal:  Antimicrob Agents Chemother       Date:  2013-11-04       Impact factor: 5.191

10.  Mycobactericidal activity of sutezolid (PNU-100480) in sputum (EBA) and blood (WBA) of patients with pulmonary tuberculosis.

Authors:  Robert S Wallis; Rodney Dawson; Sven O Friedrich; Amour Venter; Darcy Paige; Tong Zhu; Annette Silvia; Jason Gobey; Craig Ellery; Yao Zhang; Kathleen Eisenach; Paul Miller; Andreas H Diacon
Journal:  PLoS One       Date:  2014-04-14       Impact factor: 3.240
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  3 in total

1.  Comparing and Validating Machine Learning Models for Mycobacterium tuberculosis Drug Discovery.

Authors:  Thomas Lane; Daniel P Russo; Kimberley M Zorn; Alex M Clark; Alexandru Korotcov; Valery Tkachenko; Robert C Reynolds; Alexander L Perryman; Joel S Freundlich; Sean Ekins
Journal:  Mol Pharm       Date:  2018-04-26       Impact factor: 4.939

2.  In Vitro and In Vivo Activity of Oxazolidinone Candidate OTB-658 against Mycobacterium tuberculosis.

Authors:  Shaochen Guo; Bin Wang; Lei Fu; Xi Chen; Weiyan Zhang; Haihong Huang; Yu Lu
Journal:  Antimicrob Agents Chemother       Date:  2021-08-16       Impact factor: 5.191

3.  Efficient and stereoselective one-pot synthesis of benzo[b]oxazolo[3,4-d][1,4]oxazin-1-ones.

Authors:  Hongyi Zhao; Wenting Zhao; Shihao Cheng; Haijia Lu; Dongfeng Zhang; Haihong Huang
Journal:  RSC Adv       Date:  2020-06-23       Impact factor: 3.361
  3 in total

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