Synthesis and antioxidant activity evaluation of new hexahydropyrimido[5,4- c]quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4- c]quinoline-5-ones obtained by Biginelli reaction in two steps

New hexahydropyrimido[5,4- c]quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4- c]quinoline-5-ones were prepared in two steps from ethyl 4-phenyl-6-methyl-2-oxo tetrahydropyrimidine-5-carboxylates or 4-phenyl-6-methyl-2-thioxotetrahydropyrimidine-5-carboxylates, previously prepared by Biginelli...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2008-06, Vol.43 (6), p.1270-1275
Main Authors: Ismaili, Lhassane, Nadaradjane, Arulraj, Nicod, Laurence, Guyon, Catherine, Xicluna, Alain, Robert, Jean-François, Refouvelet, Bernard
Format: Article
Language:English
Subjects:
Antioxidants
Antioxidants - chemical synthesis
Antioxidants - pharmacology
Biginelli reaction
Biological and medical sciences
DPPH
Free Radical Scavengers
Free Radical Scavengers - chemical synthesis
Free Radical Scavengers - pharmacology
Hydroxyl Radical
Hydroxyl Radical - chemistry
Life Sciences
Magnetic Resonance Spectroscopy
Medical sciences
Miscellaneous
Pharmaceutical sciences
Pharmacology. Drug treatments
Quinoline
Quinolones
Quinolones - chemical synthesis
Quinolones - pharmacology
Spectrophotometry, Infrared
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Summary:New hexahydropyrimido[5,4- c]quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4- c]quinoline-5-ones were prepared in two steps from ethyl 4-phenyl-6-methyl-2-oxo tetrahydropyrimidine-5-carboxylates or 4-phenyl-6-methyl-2-thioxotetrahydropyrimidine-5-carboxylates, previously prepared by Biginelli reaction using appropriate aldehyde, urea derivatives and ethyl acetoacetate. Their antioxidant properties were evaluated by two methods: scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and scavenging effect on hydroxyl radicals. The results show that the compounds containing thiourea moiety have better activity. [Display omitted] Several hexahydropyrimido[5,4- c] quinoline-2,5-diones and 2-thioxohexahydropyrimido[5,4- c]quinoline-5-ones were prepared and evaluated for their antioxidant properties.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2007.07.012