One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (-)-β-pinene

Bioorganic & Medicinal Chemistry Letters
Shengliang LiaoZhanqian Song

Abstract

A series of novel 3-cyanopyridine derivatives of (-)-β-pinene were designed and synthesized by one-pot four-component domino reactions. The targeted compounds were evaluated for their antimicrobial activity against four bacteria (Klebsiella pneumoniae, Enterobacter aerogenes, Staphylococcus aureus, Staphylococcus epidermidis) and a fungus (Candida albicans). The results showed that most of the minimal inhibitory concentrations (MICs) of these 3-cyanopyridine derivatives against the tested strains was in the range of 15.6-125 mg/L. Among these 3-cyanopyridine derivatives, the MICs of compound 5h against S. epidermidis and C. albicans were 15.6 mg/L, which revealed that compound 5h featured double fluoro substituents at meta- and para-position was the most active compound. In addition, the preliminary structure-activity relationship analysis indicated that the change of substituents on the pyridine ring and benzene ring of 3-cyanopyridine derivatives was an important factor for inducing antimicrobial activity. This research would promote the development of heterocyclic derivatives of β-pinene with antimicrobial activity.

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May 29, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana Cristina Rivas da SilvaDaniela Sales Alviano
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Citations

Apr 23, 2017·Bioorganic & Medicinal Chemistry Letters·Yunyun WangShifa Wang
May 10, 2019·Molecular Carcinogenesis·Lingyuan XuXiaoying Huang
Sep 1, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yunfei ShiShengliang Liao
Nov 1, 2017·Journal of Food Science and Technology·Deepak Kadam, S S Lele
Nov 20, 2019·Biomolecules·Bahare SalehiJavad Sharifi-Rad
Apr 10, 2019·Chemical Reviews·Isravel MuthukrishnanJ Carlos Menéndez

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