One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (−)-β-pinene. Issue 6 (15th March 2016)

• Record Type: Journal Article
• Authors: Liao, Shengliang; Shang, Shibin; Shen, Minggui; Rao, Xiaoping; Si, Hongyan; Song, Jie; Song, Zhanqian
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 6(2016)
• Page Start: 1512
• Page End: 1515
• Publication Date: 2016-03-15
• Subjects: β-Pinene -- Nopinone -- Synthesis -- 3-Cyanopyridine -- Antimicrobial; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.02.024
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: A series of novel 3-cyanopyridine compounds were synthesized from the natural resource β-pinene, and their antimicrobial activities were evaluated. 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 compound5h against S. epidermidis and C. albicans were 15.6 mg/L, which revealed that compound5h 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.