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Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach

[Image: see text] An efficient taurine-catalyzed green multicomponent approach has been described for the first time to synthesize densely substituted therapeutic core dihydropyrano[2,3-c]pyrazoles. Applications of the developed synthetic strategies and technologies revealed the synthesis of a serie...

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Autores principales: Mali, Ghanshyam, Shaikh, Badrodin A., Garg, Shivani, Kumar, Akhilesh, Bhattacharyya, Sudipta, Erande, Rohan D., Chate, Asha V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600639/
https://www.ncbi.nlm.nih.gov/pubmed/34805701
http://dx.doi.org/10.1021/acsomega.1c04773
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author Mali, Ghanshyam
Shaikh, Badrodin A.
Garg, Shivani
Kumar, Akhilesh
Bhattacharyya, Sudipta
Erande, Rohan D.
Chate, Asha V.
author_facet Mali, Ghanshyam
Shaikh, Badrodin A.
Garg, Shivani
Kumar, Akhilesh
Bhattacharyya, Sudipta
Erande, Rohan D.
Chate, Asha V.
author_sort Mali, Ghanshyam
collection PubMed
description [Image: see text] An efficient taurine-catalyzed green multicomponent approach has been described for the first time to synthesize densely substituted therapeutic core dihydropyrano[2,3-c]pyrazoles. Applications of the developed synthetic strategies and technologies revealed the synthesis of a series of newly designed 1,4-dihydropyrano[2,3-c]pyrazoles containing isonicotinamide, spirooxindole, and indole moieties. Detailed in silico analysis of the synthesized analogues revealed their potential to bind wild-type and antibiotic-resistant variants of dihydrofolate reductase, a principal drug target enzyme for emerging antibiotic-resistant pathogenic Staphylococcus aureus strains. Hence, the synthesized dihydropyrano[2,3-c]pyrazole derivatives presented herein hold immense promise to develop future antistaphylococcal therapeutic agents.
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spelling pubmed-86006392021-11-19 Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach Mali, Ghanshyam Shaikh, Badrodin A. Garg, Shivani Kumar, Akhilesh Bhattacharyya, Sudipta Erande, Rohan D. Chate, Asha V. ACS Omega [Image: see text] An efficient taurine-catalyzed green multicomponent approach has been described for the first time to synthesize densely substituted therapeutic core dihydropyrano[2,3-c]pyrazoles. Applications of the developed synthetic strategies and technologies revealed the synthesis of a series of newly designed 1,4-dihydropyrano[2,3-c]pyrazoles containing isonicotinamide, spirooxindole, and indole moieties. Detailed in silico analysis of the synthesized analogues revealed their potential to bind wild-type and antibiotic-resistant variants of dihydrofolate reductase, a principal drug target enzyme for emerging antibiotic-resistant pathogenic Staphylococcus aureus strains. Hence, the synthesized dihydropyrano[2,3-c]pyrazole derivatives presented herein hold immense promise to develop future antistaphylococcal therapeutic agents. American Chemical Society 2021-11-02 /pmc/articles/PMC8600639/ /pubmed/34805701 http://dx.doi.org/10.1021/acsomega.1c04773 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Mali, Ghanshyam
Shaikh, Badrodin A.
Garg, Shivani
Kumar, Akhilesh
Bhattacharyya, Sudipta
Erande, Rohan D.
Chate, Asha V.
Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach
title Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach
title_full Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach
title_fullStr Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach
title_full_unstemmed Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach
title_short Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano[2,3-c]pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach
title_sort design, synthesis, and biological evaluation of densely substituted dihydropyrano[2,3-c]pyrazoles via a taurine-catalyzed green multicomponent approach
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600639/
https://www.ncbi.nlm.nih.gov/pubmed/34805701
http://dx.doi.org/10.1021/acsomega.1c04773
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