The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: modifications at C12 and C7

Wen-Ming Zhang; Teng Yang; Xue-Ying Pan; Xin-Lan Liu; Hai-Xia Lin; Zhao-Bing Gao; Cai-Guang Yang; Yong-Mei Cui

doi:10.1016/j.ejmech.2016.11.002

The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: modifications at C12 and C7

Eur J Med Chem. 2017 Feb 15:127:917-927. doi: 10.1016/j.ejmech.2016.11.002. Epub 2016 Nov 3.

Authors

Wen-Ming Zhang¹, Teng Yang², Xue-Ying Pan³, Xin-Lan Liu¹, Hai-Xia Lin¹, Zhao-Bing Gao⁴, Cai-Guang Yang⁵, Yong-Mei Cui⁶

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center, College of Sciences, Shanghai University, Shanghai 200444, China.
² 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.
³ Nano Science and Technology Institute, University of Science and Technology of China, Suzhou, 215123 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@t.shu.edu.cn.

PMID: 27837995
DOI: 10.1016/j.ejmech.2016.11.002

Abstract

A series of 7-N-acylaminoethyl/propyloxime 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 trifluoromethyl phenyl/benzyl, halogen-substituted thiophenyl, benzothiophenyl or pyrrolyl moiety exhibited potent in vitro antibacterial activity. Among which, compounds 4m, 4x and 7j showed high antibacterial activity with minimum inhibitory concentration (MIC) values of 1.25-3.13 μg/mL against five multidrug-resistant S. aureus.

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

MeSH terms

Abietanes / chemical synthesis*
Abietanes / chemistry
Abietanes / pharmacology*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Chemistry Techniques, Synthetic
Drug Design*
Drug Resistance, Multiple / drug effects
Staphylococcus aureus / drug effects*
Structure-Activity Relationship

Substances

Abietanes
Anti-Bacterial Agents
dehydroabietic acid