Synthesis and identification of β-aryloxyquinolines and their pyrano[3,2-c]chromene derivatives as a new class of antimicrobial and antituberculosis agents

A new class of β-aryloxyquinolines 3a–i and their pyrano[3,2-c]chromene derivatives 6a–r incorporating a validated molecular target has been synthesized via a nucleophilic displacement and a one-pot multicomponent reaction respectively. In vitro antimicrobial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Escherichia coli, Salmonella typhi, Vibrio cholera, Aspergillus fumigatus and Candida albicans. Compounds 3c, 3e, 3g, 6f, 6l and 6q exhibited excellent antibacterial activity while compound 6p exhibited more potent antifungal activity than that of first line standard drugs. In vitro antituberculosis activity was evaluated against Mycobacterium tuberculosis H37Rv and compound 6f is emerged as the promising antimicrobial member with better antitubercular activity. Majority of the compounds appears to be better antimicrobials but poor antituberculars.

Graphical abstractA series of β-aryloxyquinolines 3a–3i and their pyrano[3,2-c]chromene derivatives 6a–6r have been synthesized and compared pharmacologically concerning their antimicrobial activities as well as antituberculosis activity against H37Rv.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A series of β-aryloxyquinolines 3a–3i and their pyrano[3,2-c]chromene derivatives 6a–6r have been synthesized and compared pharmacologically concerning their antimicrobial activities as well as antituberculosis activity against H37Rv.