Molecules 2011, 16(3), 1956-1972; doi:10.3390/molecules16031956
Article

Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity

1 Departments of Photochemistry, National Research Center, 12622 Dokki, Giza, Egypt 2 Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt Current Address: Department of Chemistry, Faculty of Science, Jazan University, 2097 Jazan, Saudi Arabia. Current Address: Department of Chemistry, Faculty of Science, Taif University, Taif, Saudi Arabia.
* Author to whom correspondence should be addressed.
Received: 17 January 2011; in revised form: 11 February 2011 / Accepted: 17 February 2011 / Published: 25 February 2011
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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Abstract: 6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a–d. Reaction of 3a–d with phosphorus oxychloride yielded 6-chlorofurochromenylidenepyrimidinamines 4a–d, which were reacted with secondary amines to afford furochromenylideneamino-2,6-disubstituted pyrimidin-4-ones 5a–d. In addition, reaction of 5a–d with 3-chloropentane-2,4-dione gave 3-chloro-furochromenylpyrimidopyrimidines 6a–d. The latter were reacted with piperazine and morpholine to give 1-(furochromenyl)-pyrimidopyrimidine-3,6,8-triylpiperazines or -3,6,8-triylmorpholines 7a–d. The chemical structures of the newly synthesized compound ware characterized by IR, 1H-NMR, 13C-NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of them, particularly 3–7, exhibited promising activities.
Keywords: khellin; visnagen; furochromones; anti-inflammatory and analgesic activity

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MDPI and ACS Style

Abu-Hashem, A.A.; Youssef, M.M. Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity. Molecules 2011, 16, 1956-1972.

AMA Style

Abu-Hashem AA, Youssef MM. Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity. Molecules. 2011; 16(3):1956-1972.

Chicago/Turabian Style

Abu-Hashem, Ameen Ali; Youssef, Mohamed M. 2011. "Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-Inflammatory and Analgesic Activity." Molecules 16, no. 3: 1956-1972.

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