The semi-synthesis, biological evaluation and docking analysis of the oxime, hydrazine and hydrazide derivatives of platensimycin

Youchao Deng; Dingding Kang; Jie Shi; Wenqing Zhou; Aijun Sun; Jianhua Ju; Xiangcheng Zhu; Ben Shen; Yanwen Duan; Yong Huang

doi:10.1039/C8MD00081F

The semi-synthesis, biological evaluation and docking analysis of the oxime, hydrazine and hydrazide derivatives of platensimycin†

Youchao Deng,^a Dingding Kang,^a Jie Shi,^a Wenqing Zhou,^a Aijun Sun,^d Jianhua Ju,

^d Xiangcheng Zhu,^ab Ben Shen,

*^ae Yanwen Duan*^abc and Yong Huang

*^ac

Author affiliations

* Corresponding authors

^a Xiangya International Academy of Translational Medicine at Central South University, Changsha, Hunan 410013, China
E-mail: ywduan66@yahoo.com, jonghuang@csu.edu.cn

^b Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Changsha, Hunan 410011, China

^c National Engineering Research Center of Combinatorial Biosynthesis for Drug Discovery, Changsha, Hunan 410011, China

^d CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China

^e Departments of Chemistry and Molecular Medicine, and Natural Products Library Initiative at The Scripps Research Institute, The Scripps Research Institute, Jupiter, Florida 33458, USA
E-mail: shenb@scripps.edu

Abstract

A dozen oxime, hydrazine and hydrazide derivatives of platensimycin (PTM) analogues were synthesized, some of which showed strong antibacterial activities and were shown to be stable under the bioassay conditions. Docking analysis revealed that they have certain new interactions with β-ketoacyl-[acyl carrier protein] synthase II (FabF), suggesting that Schiff base formation on its terpene scaffold is an effective strategy to diversify PTM structure.

MedChemComm

The semi-synthesis, biological evaluation and docking analysis of the oxime, hydrazine and hydrazide derivatives of platensimycin†

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The semi-synthesis, biological evaluation and docking analysis of the oxime, hydrazine and hydrazide derivatives of platensimycin

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