Synthesis and evaluation of novel substituted 1,2,3-triazolyldihydroquinolines as promising antitubercular agents |
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| Authors: | Sandeep Kumar Marvadi Vagolu Siva Krishna Dharmarajan Sriram Srinivas Kantevari |
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| Institution: | 1. Fluoro & Agrochemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India;2. Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India;3. Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India |
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| Abstract: | A series of novel substituted 1,2,3-triazolyldihydroquinolines 6a–o was designed and synthesized from 2-acetylthiophene in five-step reaction sequence involving modified Boltzmann-Rahtz reaction of β-Enaminone; Vilsmeier-Haack chloroformylation using DMF/POCl3; Ohira-Bestmann homologation of aldehyde to alkyne as key steps. The reaction of alkyne 4 with various aryl azides in the presence of copper sulfate and sodium ascorbate resulted desired new 1,2,3-triazolyldihydroquinolines 6a–o in excellent yields. In vitro screening of new compounds for anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (Mtb), resulted in three derivatives 6a (MIC:1.56?µg/mL) and 6d, 6l (MIC:3.12?µg/mL) as promising antitubercular agents with lower cytotoxicity profiles. |
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| Keywords: | Thiophene Triazole Dihydroquinoline Corresponding author at: Fluoro & Agrochemicals Division CSIR-Indian Institute of Chemical Technology Hyderabad 500007 Telangana India |
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