Synthesis and Antitubercular Activity of 2‐(substituted phenyl/benzyl‐amino)‐6‐(4‐chlorophenyl)‐5‐(methoxycarbonyl)‐4‐methyl‐3,6‐dihydropyrimidin‐1‐ium Chlorides |
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| Authors: | Venugopala K Narayanaswamy Susanta K Nayak Melendhran Pillay Renuka Prasanna Yacoob M Coovadia Bharti Odhav |
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| Institution: | 1. Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa;2. Center for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3‐20133 Milan, Italy;3. Department of Microbiology, National Health Laboratory Services, KZN Academic Complex, Inkosi Albert Luthuli Central Hospital, Durban 4001, South Africa;4. Department of Polymer Science & Technology, Sri Krishnadevaraya University, Anantapur 515055, India |
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| Abstract: | A series of 2‐(substituted phenyl/benzyl‐amino)‐6‐(4‐chlorophenyl)‐5‐(methoxycarbonyl)‐4‐methyl‐3,6‐dihydropyrimidin‐1‐ium chlorides 7–13 and 15 was synthesized in their hydrochloride salt form. The title compounds were characterized by FT‐IR, NMR (1H and 13C) and elemental analysis. They were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv, multidrug resistance tuberculosis and extensively drug resistance tuberculosis by agar diffusion method and tested for the cytotoxic action on peripheral blood mononuclear cells by MTT assay. Among all the tested compounds in the series, compounds 7 and 11 emerged as promising antitubercular agents at 16 μg/mL against multidrug resistance tuberculosis and over 64 μg/mL against extensively drug resistance tuberculosis. The conformational features and supramolecular assembly of the promising compounds 7 and 11 were determined by single crystal X‐ray study. |
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| Keywords: | anti‐TB activity cytotoxicity dihydropyrimidine single crystal X‐ray crystallography |
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