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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Autores principales: Nelson, Grady L., Williams, Michael J., Jonnalagadda, Shirisha, Alam, Mohammad A., Mereddy, Gautam, Johnson, Joseph L., Jonnalagadda, Sravan K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi 2018
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6206569/
https://www.ncbi.nlm.nih.gov/pubmed/30410798
http://dx.doi.org/10.1155/2018/5758076
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author Nelson, Grady L.
Williams, Michael J.
Jonnalagadda, Shirisha
Alam, Mohammad A.
Mereddy, Gautam
Johnson, Joseph L.
Jonnalagadda, Sravan K.
author_facet Nelson, Grady L.
Williams, Michael J.
Jonnalagadda, Shirisha
Alam, Mohammad A.
Mereddy, Gautam
Johnson, Joseph L.
Jonnalagadda, Sravan K.
author_sort Nelson, Grady L.
collection PubMed
description 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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spelling pubmed-62065692018-11-08 Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents Nelson, Grady L. Williams, Michael J. Jonnalagadda, Shirisha Alam, Mohammad A. Mereddy, Gautam Johnson, Joseph L. Jonnalagadda, Sravan K. Int J Med Chem Research Article 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. Hindawi 2018-10-16 /pmc/articles/PMC6206569/ /pubmed/30410798 http://dx.doi.org/10.1155/2018/5758076 Text en Copyright © 2018 Grady L. Nelson et al. https://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Nelson, Grady L.
Williams, Michael J.
Jonnalagadda, Shirisha
Alam, Mohammad A.
Mereddy, Gautam
Johnson, Joseph L.
Jonnalagadda, Sravan K.
Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents
title Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents
title_full Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents
title_fullStr Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents
title_full_unstemmed Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents
title_short Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents
title_sort synthesis and evaluation of baylis-hillman reaction derived imidazole and triazole cinnamates as antifungal agents
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6206569/
https://www.ncbi.nlm.nih.gov/pubmed/30410798
http://dx.doi.org/10.1155/2018/5758076
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