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Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents
Herein, a new series of N-substituted 1,2,3-triazolylmethyl indole derivatives 4(a–u) was synthesized by rationally incorporating a pharmacophoric active heterocyclic ring containing indole and triazole moieties in one molecular frame via the conventional and microwave irradiation methods. Briefly,...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9761696/ https://www.ncbi.nlm.nih.gov/pubmed/36545291 http://dx.doi.org/10.1039/d2ra05960f |
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author | Ashok, Dongamanti Thara, Gugulothu Kumar, Bhukya Kiran Srinivas, Gundu Ravinder, Dharavath Vishnu, Thumma Sarasija, Madderla Sushmitha, Bujji |
author_facet | Ashok, Dongamanti Thara, Gugulothu Kumar, Bhukya Kiran Srinivas, Gundu Ravinder, Dharavath Vishnu, Thumma Sarasija, Madderla Sushmitha, Bujji |
author_sort | Ashok, Dongamanti |
collection | PubMed |
description | Herein, a new series of N-substituted 1,2,3-triazolylmethyl indole derivatives 4(a–u) was synthesized by rationally incorporating a pharmacophoric active heterocyclic ring containing indole and triazole moieties in one molecular frame via the conventional and microwave irradiation methods. Briefly, the new compounds 4(a–u) were synthesized via the N-alkylation of tetrahydro-1H-carbazoles followed by click reaction and copper-catalyzed Huisgen [3 + 2] cycloaddition in the presence of copper sulphate and sodium ascorbate with various aromatic azides 3(a–m). All the newly synthesized compounds were characterized via(1)H and (13)C NMR, mass, and IR spectroscopy and evaluated for their antimicrobial, antioxidant and anticancer activities. Among the synthesized compounds, 4d, 4j, 4n, 4p, 4s and 4r were found to exhibit good antimicrobial, antioxidant, anticancer activities. The biological activity of the synthesized compounds was further supplemented by molecular docking studies against the target receptors caspase-3 and 17-beta-hydroxy steroid dehydrogenase type 1, revealing that the reported structures best fit into the active site pocket of the target molecules. |
format | Online Article Text |
id | pubmed-9761696 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-97616962022-12-20 Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents Ashok, Dongamanti Thara, Gugulothu Kumar, Bhukya Kiran Srinivas, Gundu Ravinder, Dharavath Vishnu, Thumma Sarasija, Madderla Sushmitha, Bujji RSC Adv Chemistry Herein, a new series of N-substituted 1,2,3-triazolylmethyl indole derivatives 4(a–u) was synthesized by rationally incorporating a pharmacophoric active heterocyclic ring containing indole and triazole moieties in one molecular frame via the conventional and microwave irradiation methods. Briefly, the new compounds 4(a–u) were synthesized via the N-alkylation of tetrahydro-1H-carbazoles followed by click reaction and copper-catalyzed Huisgen [3 + 2] cycloaddition in the presence of copper sulphate and sodium ascorbate with various aromatic azides 3(a–m). All the newly synthesized compounds were characterized via(1)H and (13)C NMR, mass, and IR spectroscopy and evaluated for their antimicrobial, antioxidant and anticancer activities. Among the synthesized compounds, 4d, 4j, 4n, 4p, 4s and 4r were found to exhibit good antimicrobial, antioxidant, anticancer activities. The biological activity of the synthesized compounds was further supplemented by molecular docking studies against the target receptors caspase-3 and 17-beta-hydroxy steroid dehydrogenase type 1, revealing that the reported structures best fit into the active site pocket of the target molecules. The Royal Society of Chemistry 2022-12-19 /pmc/articles/PMC9761696/ /pubmed/36545291 http://dx.doi.org/10.1039/d2ra05960f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Ashok, Dongamanti Thara, Gugulothu Kumar, Bhukya Kiran Srinivas, Gundu Ravinder, Dharavath Vishnu, Thumma Sarasija, Madderla Sushmitha, Bujji Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
title | Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
title_full | Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
title_fullStr | Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
title_full_unstemmed | Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
title_short | Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
title_sort | microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9761696/ https://www.ncbi.nlm.nih.gov/pubmed/36545291 http://dx.doi.org/10.1039/d2ra05960f |
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