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Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents.

ABSTRACT: Allylic acetates derived from Baylis-Hillman reaction undergo efficient nucleophilic isomerization with imidazoles and triazoles to provide imidazolylmethyl and triazolylmethyl cinnamates stereoselectively. Antifungal evaluation of these derivatives against Cryptococcus neoformans exhibits good minimum inhibitory concentration values. These compounds exhibit low toxicity in proliferating MCF-7 breast cancer cell line. Structure activity relationship studies indicate that halogenated aromatic derivatives provide better antifungal activity.

SUBMITTER: Nelson GL

PROVIDER: S-EPMC6206569 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents.

Nelson Grady L GL Williams Michael J MJ Jonnalagadda Shirisha S Alam Mohammad A MA Mereddy Gautam G Johnson Joseph L JL Jonnalagadda Sravan K SK

International journal of medicinal chemistry 20181016

Allylic acetates derived from Baylis-Hillman reaction undergo efficient nucleophilic isomerization with imidazoles and triazoles to provide imidazolylmethyl and triazolylmethyl cinnamates stereoselectively. Antifungal evaluation of these derivatives against <i>Cryptococcus neoformans</i> exhibits good minimum inhibitory concentration values. These compounds exhibit low toxicity in proliferating MCF-7 breast cancer cell line. Structure activity relationship studies indicate that halogenated aroma ...[more]

PMID: 30410798

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