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通过两步法Biginelli反应得到的新型六氢嘧啶并[5,4-c]喹啉-2,5-二酮和2-硫代六氢嘧啶并[5,4-c]喹啉-5-酮的合成及抗氧化活性评价

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.

作者信息

Ismaili Lhassane, Nadaradjane Arulraj, Nicod Laurence, Guyon Catherine, Xicluna Alain, Robert Jean-François, Refouvelet Bernard

机构信息

Equipe Sciences séparatives et Biopharmaceutique (2SB), Laboratoire de chimie thérapeutique, Faculté de Medecine et de Pharmacie, 4, place Saint Jacques - 25030 Besançon Cedex, France.

出版信息

Eur J Med Chem. 2008 Jun;43(6):1270-5. doi: 10.1016/j.ejmech.2007.07.012. Epub 2007 Aug 2.

Abstract

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.

摘要

新型六氢嘧啶并[5,4-c]喹啉-2,5-二酮和2-硫代六氢嘧啶并[5,4-c]喹啉-5-酮由4-苯基-6-甲基-2-氧代四氢嘧啶-5-羧酸乙酯或4-苯基-6-甲基-2-硫代四氢嘧啶-5-羧酸乙酯分两步制备,上述乙酯先前通过使用适当醛、尿素衍生物和乙酰乙酸乙酯的Biginelli反应制备。通过两种方法评估了它们的抗氧化性能:对2,2-二苯基-1-苦基肼基(DPPH)自由基的清除作用和对羟基自由基的清除作用。结果表明,含有硫脲部分的化合物具有更好的活性。

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