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One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (-)-β-pinene.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2016 Mar 15; Vol. 26 (6), pp. 1512-1515. Date of Electronic Publication: 2016 Feb 10. - Publication Year :
- 2016
-
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.<br /> (Copyright © 2016. Published by Elsevier Ltd.)
- Subjects :
- Anti-Bacterial Agents chemistry
Antifungal Agents chemistry
Bacteria drug effects
Bicyclic Monoterpenes
Bridged Bicyclo Compounds chemical synthesis
Dose-Response Relationship, Drug
Fungi drug effects
Microbial Sensitivity Tests
Molecular Structure
Monoterpenes chemical synthesis
Pyridines pharmacology
Stereoisomerism
Structure-Activity Relationship
Anti-Bacterial Agents chemical synthesis
Anti-Bacterial Agents pharmacology
Antifungal Agents chemical synthesis
Antifungal Agents pharmacology
Bridged Bicyclo Compounds chemistry
Bridged Bicyclo Compounds pharmacology
Monoterpenes chemistry
Monoterpenes pharmacology
Pyridines chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 26
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 26898336
- Full Text :
- https://doi.org/10.1016/j.bmcl.2016.02.024