1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluationElectronic supplementary information (ESI) available. CCDC 1820092. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ra03197e

• Main Authors: Ashok, Dongamanti, Chiranjeevi, Pamula, Kumar, Aamate Vikas, Sarasija, Madderla, Krishna, Vagolu Siva, Sriram, Dharmarajan, Balasubramanian, Sridhar
• Format: Article
• Language: English
• ISSN: 2046-2069
• DOI: 10.1039/c8ra03197e

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. A convenient synthesis of novel prototypes containing the two pharmacophores of chromene and 1,2,3-triazole in a single molecular backbone, were evaluated against Mycobacterium tuberculosis H37Rv strain.