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Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst

An efficient and green method has been developed for the synthesis of new substituted Hantzsch thiazole derivatives in 79%–90% yield, via the one-pot multi-component procedure, by the reaction of 3-(bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiourea and substituted benzaldehydes in the presenc...

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Autores principales: Bouherrou, Houria, Saidoun, Aicha, Abderrahmani, Ahmed, Abdellaziz, Lamia, Rachedi, Yahia, Dumas, Françoise, Demenceau, Albert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6153747/
https://www.ncbi.nlm.nih.gov/pubmed/28481282
http://dx.doi.org/10.3390/molecules22050757
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author Bouherrou, Houria
Saidoun, Aicha
Abderrahmani, Ahmed
Abdellaziz, Lamia
Rachedi, Yahia
Dumas, Françoise
Demenceau, Albert
author_facet Bouherrou, Houria
Saidoun, Aicha
Abderrahmani, Ahmed
Abdellaziz, Lamia
Rachedi, Yahia
Dumas, Françoise
Demenceau, Albert
author_sort Bouherrou, Houria
collection PubMed
description An efficient and green method has been developed for the synthesis of new substituted Hantzsch thiazole derivatives in 79%–90% yield, via the one-pot multi-component procedure, by the reaction of 3-(bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiourea and substituted benzaldehydes in the presence of silica supported tungstosilisic acid, as a reusable catalyst, under conventional heating or under ultrasonic irradiation. The catalyst is recoverable by a simple filtration and can be reused in the subsequent reactions. Most of the thiazoles exhibited significant antibacterial activity compared toamoxicillin and ciprofloxacin as positive controls. In addition, the new compounds showed moderate to good antioxidant (DPPH) radical scavenging activity.
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spelling pubmed-61537472018-11-13 Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst Bouherrou, Houria Saidoun, Aicha Abderrahmani, Ahmed Abdellaziz, Lamia Rachedi, Yahia Dumas, Françoise Demenceau, Albert Molecules Article An efficient and green method has been developed for the synthesis of new substituted Hantzsch thiazole derivatives in 79%–90% yield, via the one-pot multi-component procedure, by the reaction of 3-(bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiourea and substituted benzaldehydes in the presence of silica supported tungstosilisic acid, as a reusable catalyst, under conventional heating or under ultrasonic irradiation. The catalyst is recoverable by a simple filtration and can be reused in the subsequent reactions. Most of the thiazoles exhibited significant antibacterial activity compared toamoxicillin and ciprofloxacin as positive controls. In addition, the new compounds showed moderate to good antioxidant (DPPH) radical scavenging activity. MDPI 2017-05-07 /pmc/articles/PMC6153747/ /pubmed/28481282 http://dx.doi.org/10.3390/molecules22050757 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bouherrou, Houria
Saidoun, Aicha
Abderrahmani, Ahmed
Abdellaziz, Lamia
Rachedi, Yahia
Dumas, Françoise
Demenceau, Albert
Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst
title Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst
title_full Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst
title_fullStr Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst
title_full_unstemmed Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst
title_short Synthesis and Biological Evaluation of New Substituted Hantzsch Thiazole Derivatives from Environmentally Benign One-Pot Synthesis Using Silica Supported Tungstosilisic Acid as Reusable Catalyst
title_sort synthesis and biological evaluation of new substituted hantzsch thiazole derivatives from environmentally benign one-pot synthesis using silica supported tungstosilisic acid as reusable catalyst
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6153747/
https://www.ncbi.nlm.nih.gov/pubmed/28481282
http://dx.doi.org/10.3390/molecules22050757
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