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Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach

An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N...

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Autores principales: Khan, Mohd. Shahnawaz, Agrawal, Ranu, Ubaidullah, Mohammad, Hassan, Md. Imtaiyaz, Tarannum, Nazia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6806407/
https://www.ncbi.nlm.nih.gov/pubmed/31692746
http://dx.doi.org/10.1016/j.heliyon.2019.e02615
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author Khan, Mohd. Shahnawaz
Agrawal, Ranu
Ubaidullah, Mohammad
Hassan, Md. Imtaiyaz
Tarannum, Nazia
author_facet Khan, Mohd. Shahnawaz
Agrawal, Ranu
Ubaidullah, Mohammad
Hassan, Md. Imtaiyaz
Tarannum, Nazia
author_sort Khan, Mohd. Shahnawaz
collection PubMed
description An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N-(substituted)phenyl malonic acid in the presence of a base catalyst, piperidine. All reported compounds were assessed for their antimicrobial activities which clearly suggested their therapeutic implications to address antimicrobial pathogenesis. The synthesized coumarin compounds were examined for their antimicrobial activity against 7 fungal strains and 2 bacterial strains at concentration 125–1000 μg/mL. In particular, the compounds 4 and 5 showed lower minimum inhibitory concentration value (125 μg/mL) against maximum microbial strains. Further, docking of all the synthesized compounds was performed with the enzymes lanosterol 14α-demethylase and glucosamine-6-phosphate synthase and a significant binding affinity was observed which supports in vivo antimicrobial study. In addition, the thermal analysis revealed good thermal stability of compounds up to 250 °C. The compounds showed abroad absorption spectrum between 280-550 nm establishing them to be good UV absorbers.
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spelling pubmed-68064072019-11-05 Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach Khan, Mohd. Shahnawaz Agrawal, Ranu Ubaidullah, Mohammad Hassan, Md. Imtaiyaz Tarannum, Nazia Heliyon Article An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N-(substituted)phenyl malonic acid in the presence of a base catalyst, piperidine. All reported compounds were assessed for their antimicrobial activities which clearly suggested their therapeutic implications to address antimicrobial pathogenesis. The synthesized coumarin compounds were examined for their antimicrobial activity against 7 fungal strains and 2 bacterial strains at concentration 125–1000 μg/mL. In particular, the compounds 4 and 5 showed lower minimum inhibitory concentration value (125 μg/mL) against maximum microbial strains. Further, docking of all the synthesized compounds was performed with the enzymes lanosterol 14α-demethylase and glucosamine-6-phosphate synthase and a significant binding affinity was observed which supports in vivo antimicrobial study. In addition, the thermal analysis revealed good thermal stability of compounds up to 250 °C. The compounds showed abroad absorption spectrum between 280-550 nm establishing them to be good UV absorbers. Elsevier 2019-10-18 /pmc/articles/PMC6806407/ /pubmed/31692746 http://dx.doi.org/10.1016/j.heliyon.2019.e02615 Text en © 2019 Published by Elsevier Ltd. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Khan, Mohd. Shahnawaz
Agrawal, Ranu
Ubaidullah, Mohammad
Hassan, Md. Imtaiyaz
Tarannum, Nazia
Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
title Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
title_full Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
title_fullStr Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
title_full_unstemmed Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
title_short Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
title_sort design, synthesis and validation of anti-microbial coumarin derivatives: an efficient green approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6806407/
https://www.ncbi.nlm.nih.gov/pubmed/31692746
http://dx.doi.org/10.1016/j.heliyon.2019.e02615
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