Synthesis of chloro, fluoro, and nitro derivatives of 7-amino-5-aryl-6-cyano-5H-pyrano pyrimidin-2,4-diones using organic catalysts and their antimicrobial and anticancer activities

Chloro, fluoro, and nitro derivatives of 7-amino-5-aryl-6-cyano-5H-pyrano pyrimidin-2,4-diones were produced by reacting malononitrile, barbituric acid, and aromatic aldehydes together with a DABCO catalyst in an aqueous one-pot reaction. This is the first report of these compounds being synthesized with DABCO as a catalyst, which produced the compounds in yields in excess of 90%. The 2,4-difluoro derivative (11) was novel. The structures of the synthesized compounds were elucidated by means of H-1, C-13, and 2D NMR spectroscopy. Compound 2 (2-Cl derivative) had MBC values of Staphylococcus aureus and MRSA, and the 2-nitro derivative 5 had an MBC of 191 mu M against the Gram-ve Escherichia coli. The synthesized compounds were also tested for their anticancer activity against a HeLa cell line, where all the compounds showed better activity (IC50 values between 129 mu M and 340 mu M) than 5-fluorouracil, a commonly known anticancer drug.