title: Unusual transformation of substituted-3-formylchromones to pyrimidine analogues: synthesis and antimicrobial activities of 5-(o-hydroxyaroyl)pyrimidines.
abstract: Substituted-3-formylchromones (4a-e) on reaction with 1,3-bis-dimethylaminomethylene-thiourea (5) in refluxing toluene solution give novel substituted 5-(o-hydroxyaroyl)pyrimidines (6a-e) in high yields. A mechanistic rationalization of the formation of products (6a-e) is proffered. Antimicrobial activities of all the synthesized compounds (6a-e) were evaluated against various fungal and bacterial strains. Compound 6d display significant antifungal activity (MIC 15) against Geotrichum candidum in comparison fluconazole used as positive control. Some of the compounds also display good antibacterial activity. Cytotoxic profile of compound 6d against HeLa cells indicates that at concentration (20 μM) no significant cell death (~2%) was observed.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Ropar 140 001, Punjab, India.
authors.forename: Tilak
authors.initials: T
authors.lastname: Raj
authors.forename: Narinder
authors.initials: N
authors.lastname: Singh
authors.forename: M P S
authors.initials: MP
authors.lastname: Ishar
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002175:Candida / Q000187:drug effects; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005848:Geotrichum / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D002867:Chromones; D011743:Pyrimidines; C502480:formylchromone
keywords: 3-Formylchromones; Antibacterial activities; Antifungal activities; Azadienes; Pyrimidines