title: 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 μg/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.
authors: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, Mississippi 38677, United States.
authors: Liyan
authors: L
authors: Dai
authors: Melissa R
authors: MR
authors: Jacob
authors: Shabana I
authors: SI
authors: Khan
authors: Ikhlas A
authors: IA
authors: Khan
authors: Alice M
authors: AM
authors: Clark
authors: Xing-Cong
authors: XC
authors: Li
mesh_terms: D000818:Animals; D000862:Ant Venoms / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001000:Ants; D002175:Candida / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000862:Ant Venoms; D000935:Antifungal Agents; D010880:Piperidines; D011725:Pyridines