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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.
- Source :
-
Journal of Heterocyclic Chemistry . Nov2019, Vol. 56 Issue 11, p3008-3016. 9p. - Publication Year :
- 2019
-
Abstract
- 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 1H, 13C, and 2D NMR spectroscopy. Compound 2 (2‐Cl derivative) had MBC values of <200μM against both Staphylococcus aureus and MRSA, and the 2‐nitro derivative 5 had an MBC of 191μM 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 129μM and 340μM) than 5‐fluorouracil, a commonly known anticancer drug. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 0022152X
- Volume :
- 56
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- Journal of Heterocyclic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 139742573
- Full Text :
- https://doi.org/10.1002/jhet.3695