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1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation
A facile and convenient approach has been designed for the synthesis of novel prototypes that possess the advantage of the two pharmacophores of chromene and 1,2,3-triazole in a single molecular backbone, were evaluated against Mycobacterium tuberculosis H37Rv strain. The new analogues 1,2,3-triazol...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9080333/ https://www.ncbi.nlm.nih.gov/pubmed/35540499 http://dx.doi.org/10.1039/c8ra03197e |
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author | Ashok, Dongamanti Chiranjeevi, Pamula Kumar, Aamate Vikas Sarasija, Madderla Krishna, Vagolu Siva Sriram, Dharmarajan Balasubramanian, Sridhar |
author_facet | Ashok, Dongamanti Chiranjeevi, Pamula Kumar, Aamate Vikas Sarasija, Madderla Krishna, Vagolu Siva Sriram, Dharmarajan Balasubramanian, Sridhar |
author_sort | Ashok, Dongamanti |
collection | PubMed |
description | A facile and convenient approach has been designed for the synthesis of novel prototypes that possess the advantage of the two pharmacophores of chromene and 1,2,3-triazole in a single molecular backbone, were evaluated against Mycobacterium tuberculosis H37Rv strain. The new analogues 1,2,3-triazole-fused spirochromenes were accomplished in four step synthetic strategy utilizing click chemistry ([3 + 2] Huisgen cycloaddition) in the ultimate step. The synthesized compounds were established based on the spectral data and X-ray crystal structure for 7a. Among the compounds tested against Mycobacterium tuberculosis H37Rv strain, some products exhibited potent antimycobacterial activity with minimum inhibitory concentration (MIC) values ranging from 1.56 to 6.25 μg mL(−1). Compounds exhibiting good in vitro potency in the MTB MIC assay were further examined for cytotoxicity in a RAW 264.7 cells. Compounds 7a, 7d, 7i (MIC: 1.56 μg mL(−1)) and 7k, 7m (MIC: 3.125 μg mL(−1)) exhibited promising hits. |
format | Online Article Text |
id | pubmed-9080333 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90803332022-05-09 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation Ashok, Dongamanti Chiranjeevi, Pamula Kumar, Aamate Vikas Sarasija, Madderla Krishna, Vagolu Siva Sriram, Dharmarajan Balasubramanian, Sridhar RSC Adv Chemistry A facile and convenient approach has been designed for the synthesis of novel prototypes that possess the advantage of the two pharmacophores of chromene and 1,2,3-triazole in a single molecular backbone, were evaluated against Mycobacterium tuberculosis H37Rv strain. The new analogues 1,2,3-triazole-fused spirochromenes were accomplished in four step synthetic strategy utilizing click chemistry ([3 + 2] Huisgen cycloaddition) in the ultimate step. The synthesized compounds were established based on the spectral data and X-ray crystal structure for 7a. Among the compounds tested against Mycobacterium tuberculosis H37Rv strain, some products exhibited potent antimycobacterial activity with minimum inhibitory concentration (MIC) values ranging from 1.56 to 6.25 μg mL(−1). Compounds exhibiting good in vitro potency in the MTB MIC assay were further examined for cytotoxicity in a RAW 264.7 cells. Compounds 7a, 7d, 7i (MIC: 1.56 μg mL(−1)) and 7k, 7m (MIC: 3.125 μg mL(−1)) exhibited promising hits. The Royal Society of Chemistry 2018-05-09 /pmc/articles/PMC9080333/ /pubmed/35540499 http://dx.doi.org/10.1039/c8ra03197e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Ashok, Dongamanti Chiranjeevi, Pamula Kumar, Aamate Vikas Sarasija, Madderla Krishna, Vagolu Siva Sriram, Dharmarajan Balasubramanian, Sridhar 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
title | 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
title_full | 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
title_fullStr | 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
title_full_unstemmed | 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
title_short | 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
title_sort | 1,2,3-triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9080333/ https://www.ncbi.nlm.nih.gov/pubmed/35540499 http://dx.doi.org/10.1039/c8ra03197e |
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