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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...

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Autores principales: Ashok, Dongamanti, Chiranjeevi, Pamula, Kumar, Aamate Vikas, Sarasija, Madderla, Krishna, Vagolu Siva, Sriram, Dharmarajan, Balasubramanian, Sridhar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
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.
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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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