title: Synthesis and antitubercular screening of [(2-chloroquinolin-3-yl)methyl] thiocarbamide derivatives.
abstract: A series of 1-(substituted-phenyl)-1-[(2-chloroquinolin-3-yl)methyl]thiocarbamide and 1-(substituted-phenyl)-1-[(2-chloroquinolin-3-yl)methyl]methylthiocarbamide derivatives was synthesized as antitubercular agent. The structure of quinolinyl amines and their thiocarbamide derivatives were established on the basis of IR, (1)H and (13)C-NMR and mass spectral data. All the compounds were tested in vitro for antimycobacterial activity against Mycobacterium tuberculosis (ATCC-25177) in Lowenstein-Jensen medium by well diffusion method and MIC by twofold serial dilution method. Results of the antitubercular screening revealed that compounds showed moderate to good antitubercular activity. Compound having two halogens in the phenyl rings viz. 3g, 3h, 4g, and 4h exhibited MIC of 50 μg/mL. The computational parameters relevant to absorption and permeation of target compounds were also calculated and found to be well correlated with antitubercular activity.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi, 110062, India.
authors.forename: Suresh
authors.initials: S
authors.lastname: Kumar
authors.forename: Neeraj
authors.initials: N
authors.lastname: Upmanyu
authors.forename: Obaid
authors.initials: O
authors.lastname: Afzal
authors.forename: Sandhya
authors.initials: S
authors.lastname: Bawa
mesh_terms: D000284:Administration, Oral; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology*; D001682:Biological Availability; D060326:Chemistry Techniques, Synthetic; D002739:Chloroquinolinols / Q000737:chemistry; D004353:Drug Evaluation, Preclinical / Q000379:methods*; D005000:Ethionamide / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship; D013890:Thiourea / Q000737:chemistry
chemical_list: D000995:Antitubercular Agents; D002739:Chloroquinolinols; D013890:Thiourea; D005000:Ethionamide
keywords: 2-chloro-3-formylquinoline; Ethionamide; Lipinski's rule; antimycobacterial activity; pharmacokinetic descriptor; thiocarbamide