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

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 mini...

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Bibliographic Details
Published in:International Journal of Medicinal Chemistry (Online) 2018-01, Vol.2018, p.1-8
Main Authors: Nelson, Grady L., Williams, Michael J., Jonnalagadda, Shirisha, Alam, Mohammad A., Mereddy, Gautam, Johnson, Joseph L., Jonnalagadda, Sravan K.
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Alcohol
Antifungal activity
Antifungal agents
Bacterial infections
Breast cancer
Chemical synthesis
Derivatives
Fungicides
Imidazole
Infections
Isomerization
Life expectancy
Minimum inhibitory concentration
Mortality
Pharmaceutical sciences
Toxicity
Triazoles
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Summary: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.
ISSN:2090-2069
2090-2077
DOI:10.1155/2018/5758076