title: Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines.
abstract: A series of β-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 °C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these β-keto esters were characterized using (1)H NMR, (13)C NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity.
authors.affiliation: Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India.
authors.forename: R
authors.initials: R
authors.lastname: Venkat Ragavan
authors.forename: V
authors.initials: V
authors.lastname: Vijayakumar
authors.forename: K
authors.initials: K
authors.lastname: Rajesh
authors.forename: B
authors.initials: B
authors.lastname: Palakshi Reddy
authors.forename: S
authors.initials: S
authors.lastname: Karthikeyan
authors.forename: N
authors.initials: N
authors.lastname: Suchetha Kumari
mesh_terms: D000085:Acetates / Q000737:chemistry; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects / Q000254:growth & development; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D006801:Humans; D020128:Inhibitory Concentration 50; D007659:Ketones / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000085:Acetates; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D004952:Esters; D007659:Ketones; D012997:Solvents; C007650:ethyl acetate