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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #270859

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

item Dai, Liyan - University Of Mississippi
item Jacob, Melissa - University Of Mississippi
item Khan, Shabana - University Of Mississippi
item Khan, Ikhlas - University Of Mississippi
item Clark, Alice - University Of Mississippi
item Li, Xing-cong - University Of Mississippi

Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/15/2011
Publication Date: 9/9/2011
Citation: Dai, L., Jacob, M.R., Khan, S.I., Khan, I.A., Clark, A.M., Li, X. 2011. Synthesis and antifungal activity of natural product-based 6-alkyl-2 3 4 5-tetrahydropyridines. Journal of Natural Products. 74(9):2023-2026.

Interpretive Summary: This manuscript describes the synthesis and antifungal activity of seven fire ant venom alkaloid analogs.

Technical Abstract: Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a–5g) that mimic the natural products piperideines that were recently identified in the fire ant venom have been synthesized. Compounds 5c–5g with the 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 ones. Compound 5e exhibits minimum fungicidal concentrations (MICs) of 3.8, 15.0, 7.5, and 7.5 'g/mL against Cryptococcus neoformans, Candida albicans, C. glabrata, and C. 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 of evaluating antifungal activities of synthetic analogs of the newly identified fire ant venom alkaloids.