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. 2018 Oct 16:2018:5758076.
doi: 10.1155/2018/5758076. eCollection 2018.

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

Grady L Nelson  1 , Michael J Williams  2 , Shirisha Jonnalagadda  1 , Mohammad A Alam  2 , Gautam Mereddy  2 , Joseph L Johnson  2 , Sravan K Jonnalagadda  1
Affiliations

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

Grady L Nelson et al. Int J Med Chem. .

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.

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Figures

Figure 1
Figure 1
Few examples of imidazole and triazole based antifungal agents.
Figure 2
Figure 2
Baylis-Hillman reaction template.
Scheme 1
Scheme 1
Synthesis of 2-(imidazolylmethyl) and 2-(triazolylmethyl) cinnamates.
See this image and copyright information in PMC

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