The synthesis and antistaphylococcal activity of N-sulfonaminoethyloxime derivatives of dehydroabietic acid

Wen-Ming Zhang; Yang Yao; Teng Yang; Xue-Ying Wang; Zhen-Yun Zhu; Wen-Tao Xu; Hai-Xia Lin; Zhao-Bing Gao; Hu Zhou; Cai-Guang Yang; Yong-Mei Cui

doi:10.1016/j.bmcl.2018.03.062

The synthesis and antistaphylococcal activity of N-sulfonaminoethyloxime derivatives of dehydroabietic acid

Bioorg Med Chem Lett. 2018 Jun 1;28(10):1943-1948. doi: 10.1016/j.bmcl.2018.03.062. Epub 2018 Mar 23.

Authors

Wen-Ming Zhang¹, Yang Yao², Teng Yang³, Xue-Ying Wang¹, Zhen-Yun Zhu⁴, Wen-Tao Xu¹, Hai-Xia Lin¹, Zhao-Bing Gao⁴, Hu Zhou⁴, Cai-Guang Yang⁵, Yong-Mei Cui⁶

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center, College of Sciences, Shanghai University, Shanghai 200444, China.
² School of Life Sciences, Shanghai University, Shanghai 200444, China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
³ Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁴ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁵ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: yangcg@simm.ac.cn.
⁶ Department of Chemistry, Innovative Drug Research Center, College of Sciences, Shanghai University, Shanghai 200444, China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: ymcui@shu.edu.cn.

PMID: 29650291
DOI: 10.1016/j.bmcl.2018.03.062

Abstract

A series of N-sulfonaminoethyloxime derivatives of dehydroabietic acid were synthesized and investigated for their antibacterial activity against Staphylococcus aureus Newman strain and multidrug-resistant strains (NRS-1, NRS-70, NRS-100, NRS-108 and NRS-271). Most of the target compounds having chloro, bromo, trifluoromethyl phenyl moiety exhibited potent in vitro antistaphylococcal activity. The meta-CF₃ phenyl derivative T23 showed the highest activity with MIC of 0.39-0.78 μg/mL against S. aureus Newman, while several analogues showed similar potent antibacterial activity with MIC values between 0.78 and 1.56 μg/mL against five multidrug-resistant S. aureus. The stability of T35 in plasma of SD rat and the cellular cytotoxicity were also evaluated.

Keywords: Antistaphylococcal; Dehydroabietic acid; Multidrug-resistant; Oxime; Synthesis.

Publication types

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

MeSH terms

Abietanes / chemistry*
Animals
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / metabolism
Anti-Bacterial Agents / pharmacology
Drug Resistance, Multiple, Bacterial / drug effects
Drug Stability
Microbial Sensitivity Tests
Oximes / chemistry*
Oximes / metabolism
Oximes / pharmacology
Rats
Rats, Sprague-Dawley
Staphylococcus aureus / drug effects
Structure-Activity Relationship

Substances

Abietanes
Anti-Bacterial Agents
Oximes
dehydroabietic acid