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

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• 作者：Shengliang Liao^a ; Shibin Shang^a ; ^{shangsb@hotmail.com" class="auth_mail" title="E-mail the corresponding author} ; Minggui Shen^a ; Xiaoping Rao^a ; Hongyan Si^a ; Jie Song^b ; Zhanqian Song^a ; ^{lhssxly@hotmail.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：β-Pinene ; Nopinone ; Synthesis ; 3-Cyanopyridine ; Antimicrobial
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 March 2016
• 年：2016
• 卷：26
• 期：6
• 页码：1512-1515
• 全文大小：517 K

文摘

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.