title: One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (-)-β-pinene.
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.
authors.affiliation: Institute of Chemical Industry of Forest Products, China Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, State Forestry Administration's Key and Open Laboratory for Forest Chemical Engineering, Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, Jiangsu, China.
authors.forename: Shengliang
authors.initials: S
authors.lastname: Liao
authors.affiliation: Institute of Chemical Industry of Forest Products, China Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, State Forestry Administration's Key and Open Laboratory for Forest Chemical Engineering, Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, Jiangsu, China. Electronic address: shangsb@hotmail.com.
authors.forename: Shibin
authors.initials: S
authors.lastname: Shang
authors.affiliation: Institute of Chemical Industry of Forest Products, China Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, State Forestry Administration's Key and Open Laboratory for Forest Chemical Engineering, Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, Jiangsu, China.
authors.forename: Minggui
authors.initials: M
authors.lastname: Shen
authors.affiliation: Institute of Chemical Industry of Forest Products, China Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, State Forestry Administration's Key and Open Laboratory for Forest Chemical Engineering, Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, Jiangsu, China.
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Rao
authors.affiliation: Institute of Chemical Industry of Forest Products, China Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, State Forestry Administration's Key and Open Laboratory for Forest Chemical Engineering, Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, Jiangsu, China.
authors.forename: Hongyan
authors.initials: H
authors.lastname: Si
authors.affiliation: Department of Chemistry and Biochemistry, University of Michigan-Flint, 303E Kearsley Street, Flint, MI 48502, USA.
authors.forename: Jie
authors.initials: J
authors.lastname: Song
authors.affiliation: Institute of Chemical Industry of Forest Products, China Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, State Forestry Administration's Key and Open Laboratory for Forest Chemical Engineering, Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, Jiangsu, China. Electronic address: lhssxly@hotmail.com.
authors.forename: Zhanqian
authors.initials: Z
authors.lastname: Song
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011725:Pyridines / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds; D039821:Monoterpenes; D011725:Pyridines; C010789:beta-pinene; C020729:3-cyanopyridine
keywords: 3-Cyanopyridine; Antimicrobial; Nopinone; Synthesis; β-Pinene