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New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation

A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et(3)NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields. The present synthetic method exhibited numerous ad...

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Autores principales: Akolkar, Satish V., Nagargoje, Amol A., Krishna, Vagolu S., Sriram, Dharmarajan, Sangshetti, Jaiprakash N., Damale, Manoj, Shingate, Bapurao B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9066712/
https://www.ncbi.nlm.nih.gov/pubmed/35518861
http://dx.doi.org/10.1039/c9ra03425k
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author Akolkar, Satish V.
Nagargoje, Amol A.
Krishna, Vagolu S.
Sriram, Dharmarajan
Sangshetti, Jaiprakash N.
Damale, Manoj
Shingate, Bapurao B.
author_facet Akolkar, Satish V.
Nagargoje, Amol A.
Krishna, Vagolu S.
Sriram, Dharmarajan
Sangshetti, Jaiprakash N.
Damale, Manoj
Shingate, Bapurao B.
author_sort Akolkar, Satish V.
collection PubMed
description A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et(3)NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields. The present synthetic method exhibited numerous advantages such as mild reaction conditions, excellent product yields, minimal chemical waste, operational simplicity, shorter reaction time, and a wide range of substrate scope. The synthesized compounds were further evaluated for in vitro antifungal activity against five fungal strains, and some of the compounds displayed equivalent or greater potency than the standard drug. A molecular docking study against the modelled three-dimensional structure of cytochrome P450 lanosterol 14α-demethylase was also performed to understand the binding affinity and binding interactions of the enzyme. Furthermore, the synthesized compounds were evaluated for DPPH radical scavenging activity and antitubercular activity against Mycobacterium tuberculosis H37Rv strain.
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spelling pubmed-90667122022-05-04 New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation Akolkar, Satish V. Nagargoje, Amol A. Krishna, Vagolu S. Sriram, Dharmarajan Sangshetti, Jaiprakash N. Damale, Manoj Shingate, Bapurao B. RSC Adv Chemistry A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et(3)NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields. The present synthetic method exhibited numerous advantages such as mild reaction conditions, excellent product yields, minimal chemical waste, operational simplicity, shorter reaction time, and a wide range of substrate scope. The synthesized compounds were further evaluated for in vitro antifungal activity against five fungal strains, and some of the compounds displayed equivalent or greater potency than the standard drug. A molecular docking study against the modelled three-dimensional structure of cytochrome P450 lanosterol 14α-demethylase was also performed to understand the binding affinity and binding interactions of the enzyme. Furthermore, the synthesized compounds were evaluated for DPPH radical scavenging activity and antitubercular activity against Mycobacterium tuberculosis H37Rv strain. The Royal Society of Chemistry 2019-07-18 /pmc/articles/PMC9066712/ /pubmed/35518861 http://dx.doi.org/10.1039/c9ra03425k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Akolkar, Satish V.
Nagargoje, Amol A.
Krishna, Vagolu S.
Sriram, Dharmarajan
Sangshetti, Jaiprakash N.
Damale, Manoj
Shingate, Bapurao B.
New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation
title New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation
title_full New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation
title_fullStr New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation
title_full_unstemmed New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation
title_short New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et(3)NH][OAc]-mediated efficient synthesis and biological evaluation
title_sort new n-phenylacetamide-incorporated 1,2,3-triazoles: [et(3)nh][oac]-mediated efficient synthesis and biological evaluation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9066712/
https://www.ncbi.nlm.nih.gov/pubmed/35518861
http://dx.doi.org/10.1039/c9ra03425k
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