title: Synthesis and antitubercular activity of 2-(substituted phenyl/benzyl-amino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium chlorides.
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 ((1)H and (13)C) 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.
authors.affiliation: Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa.
authors.forename: Venugopala K
authors.initials: VK
authors.lastname: Narayanaswamy
authors.forename: Susanta K
authors.initials: SK
authors.lastname: Nayak
authors.forename: Melendhran
authors.initials: M
authors.lastname: Pillay
authors.forename: Renuka
authors.initials: R
authors.lastname: Prasanna
authors.forename: Yacoob M
authors.initials: YM
authors.lastname: Coovadia
authors.forename: Bharti
authors.initials: B
authors.lastname: Odhav
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001665:Binding Sites; D054908:Extensively Drug-Resistant Tuberculosis / Q000382:microbiology; D007963:Leukocytes, Mononuclear / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018088:Tuberculosis, Multidrug-Resistant / Q000382:microbiology
chemical_list: C586333:2-(3-bromophenylamino)-6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-3,6-dihydropyrimidin-1-ium; C586334:6-(4-chlorophenyl)-5-(methoxycarbonyl)-4-methyl-2-(3-(trifluoromethylthio)phenylamino)-3,6-dihydropyrimidin-1-ium; D000995:Antitubercular Agents; D011743:Pyrimidines