title: Design and synthesis of novel carbazole tethered pyrrole derivatives as potent inhibitors of Mycobacterium tuberculosis.
abstract: A series of novel carbazole tethered pyrrole derivatives were designed by coupling core fragments of antitubercular agents, carbazole and substituted pyrrole in single molecular architecture. The synthesis of new analogues was achieved by FeCl3 mediated one pot three component condensation of 2-nitrovinylcarbazoles with aryl or alkyl amines and dimethylacetylene dicarboxylate (DMAD). All the new analogues 5a-l and 6a-l were fully characterized by their NMR and mass spectral data. Among the twenty four new compounds screened for in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv, dimethyl 1-(4-fluorophenyl)-4-(9-methyl-9H-carbazol-3-yl)-1H-pyrrole-2,3-dicarboxylate (5b) was found to be most active with MIC 3.13μg/mL and has shown low cytotoxicity.
authors.affiliation: Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India.
authors.forename: Goverdhan
authors.initials: G
authors.lastname: Surineni
authors.affiliation: Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India.
authors.forename: Perumal
authors.initials: P
authors.lastname: Yogeeswari
authors.affiliation: Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India.
authors.forename: Dharmarajan
authors.initials: D
authors.lastname: Sriram
authors.affiliation: Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India; Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India. Electronic address: kantevari@yahoo.com.
authors.forename: Srinivas
authors.initials: S
authors.lastname: Kantevari
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002227:Carbazoles / Q000737:chemistry*; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000995:Antitubercular Agents; D002227:Carbazoles; D011758:Pyrroles; C041514:carbazole
keywords: Antimycobacterial activity; Carbazole; Molecular modification; Mycobacterium tuberculosis; Pyrrole