Synthesis, antimycobacterial and antibacterial activity of 1-(6-amino-3,5-difluoropyridin-2-yl)fluoroquinolone derivatives containing an oxime functional moiety

Ju Huang; Minghua Wang; Bin Wang; Zhaoyang Wu; Mingliang Liu; Lianshun Feng; Jun Zhang; Xiaoning Li; Yang Yang; Yu Lu

doi:10.1016/j.bmcl.2016.03.050

Synthesis, antimycobacterial and antibacterial activity of 1-(6-amino-3,5-difluoropyridin-2-yl)fluoroquinolone derivatives containing an oxime functional moiety

Bioorg Med Chem Lett. 2016 May 1;26(9):2262-7. doi: 10.1016/j.bmcl.2016.03.050. Epub 2016 Mar 14.

Authors

Ju Huang¹, Minghua Wang¹, Bin Wang², Zhaoyang Wu¹, Mingliang Liu³, Lianshun Feng¹, Jun Zhang⁴, Xiaoning Li¹, Yang Yang¹, Yu Lu⁵

Affiliations

¹ Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
² Beijing Key Laboratory of Drug Resistance Tuberculosis Research, Department of Pharmacology, Beijing Tuberculosis and Thoracic Tumor Research Institute, Beijing Chest Hospital, Capital Medical University, Beijing 101149, China.
³ Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. Electronic address: lmllyx@126.com.
⁴ Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China; Zhejiang Starry Pharmaceutical Co. Ltd, Xianju 317300, China.
⁵ Beijing Key Laboratory of Drug Resistance Tuberculosis Research, Department of Pharmacology, Beijing Tuberculosis and Thoracic Tumor Research Institute, Beijing Chest Hospital, Capital Medical University, Beijing 101149, China. Electronic address: luyu4876@hotmail.com.

PMID: 27020299
DOI: 10.1016/j.bmcl.2016.03.050

Abstract

A series of novel 1-(6-amino-3,5-difluoropyridin-2-yl)fluoroquinolone derivatives containing an oxime functional moiety were synthesized and evaluated for their biological activity. Our results reveal that compounds 9a-9c have considerable activity against both of MTB H37Rv ATCC 27294 (MICs: 3.81-7.13 μg/mL) and methicillin-sensitive Staphylococcus aureus strains (MICs: <0.008-0.5 μg/mL).

Keywords: Antibacterial activity; Antimycobacterial activity; Fluoroquinolone derivatives; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Antitubercular Agents / chemical synthesis*
Antitubercular Agents / chemistry
Antitubercular Agents / pharmacology*
Fluoroquinolones / chemical synthesis*
Fluoroquinolones / chemistry
Fluoroquinolones / pharmacology*
Oximes / chemistry*

Substances

Anti-Bacterial Agents
Antitubercular Agents
Fluoroquinolones
Oximes