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Synthesis and antifungal activity of natural product-based 6-alkyl-2,3,4,5-tetrahydropyridines.

ABSTRACT: Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a-5g) that mimic the natural piperideines that were recently identified in fire ant venom have been synthesized. Compounds 5c-5g with C-6 alkyl chain lengths from C14 to C18 showed varying degrees of antifungal activities, with 5e (6-hexadecyl-2,3,4,5-tetrahydropyridine) and 5f (6-heptadecyl-2,3,4,5-tetrahydropyridine) being the most active. Compound 5e exhibited minimum fungicidal concentrations of 3.8, 15.0, 7.5, and 7.5 ?g/mL against Cryptococcus neoformans, Candida albicans, Candida glabrata, and Candida krusei, respectively. The antifungal activities of these compounds appear to be associated with the C-6 side chain length. This study represents the first effort to evaluate antifungal activities of synthetic analogues of the newly identified fire ant venom alkaloids.

SUBMITTER: Dai L

PROVIDER: S-EPMC3189850 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Synthesis and antifungal activity of natural product-based 6-alkyl-2,3,4,5-tetrahydropyridines.

Dai Liyan L Jacob Melissa R MR Khan Shabana I SI Khan Ikhlas A IA Clark Alice M AM Li Xing-Cong XC

Journal of natural products 20110909 9

Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a-5g) that mimic the natural piperideines that were recently identified in fire ant venom have been synthesized. Compounds 5c-5g with C-6 alkyl chain lengths from C14 to C18 showed varying degrees of antifungal activities, with 5e (6-hexadecyl-2,3,4,5-tetrahydropyridine) and 5f (6-heptadecyl-2,3,4,5-tetrahydropyridine) being the most active. Compound 5e exhibited minimum fungicidal concentrations of 3.8, 15.0, 7.5, and 7.5 μg/mL against Cryptococcus ne ...[more]

PMID: 21905650

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