title: New 2-Imino-2H-Chromene-3(N-aryl)carboxamides as Potential Cytotoxic Agents.
abstract: Synthesis and structure activity relationships of four series of novel 2-imino-2H-chromene-3(N-aryl) carboxamides (V-VIII) have been described by bioisosteric replacement of usually present ketone at 2nd position of coumarin with imine. Various substitutents are introduced on aryl and chromene ring of iminocoumarin to investigate the effect of lipophilicity and electronic properties of substituents on cytotoxic activity against four human cancer cell lines. Novel 2-imino-2H-chromene-3(N-aryl)carboxamides (V-VIII) were synthesized by the reaction of substituted 2- cyanoacetamides with different salicyaldehydes in the presence of sodium acetate in glacial acetic acid. Compound VIa showed potent activity against MCF-7 (IC50 = 8.5 μM), PC-3 (IC50 = 35.0 μM), A-549 (IC50 = 0.9 μM) and Caco-2 (IC50 = 9.9 μM) cell lines. The anticancer results revealed that most of the synthesized compounds showed equipotent activity with the standard 5-fluorouracil and docetaxel on Caco-2 and MCF-7 cell lines, respectively.
authors.forename: Rupinder Kaur
authors.initials: RK
authors.lastname: Gill
authors.forename: Jyoti
authors.initials: J
authors.lastname: Kumari
authors.affiliation: Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Moga-142001, Punjab, India.
authors.forename: Jitender
authors.initials: J
authors.lastname: Bariwal
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018938:Caco-2 Cells; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D061986:MCF-7 Cells; D009369:Neoplasms / Q000188:drug therapy; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001578:Benzopyrans; D007097:Imines