Department of Photochemistry, National Research Center, 12622 Dokki, Giza, Egypt.
Molecules. 2011 Feb 25;16(3):1956-72. doi: 10.3390/molecules16031956.
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.
6-[(4-甲氧基/4,9-二甲氧基)-7-甲基呋喃并[2,3-d]色烯-5-亚氨基]氨基]-2-硫代-2,3-二氢嘧啶-4(3H)-酮 1a,b 是通过 6-氨基-2-硫代尿嘧啶分别与维斯纳根或黄木樨草素反应得到的。1a,b 与碘甲烷反应得到呋喃并[2,3-d]色烯亚氨基甲硫基嘧啶-4(3H)-酮 2a,b。化合物 2a,b 与仲脂肪族胺反应得到相应的呋喃并[2,3-d]色烯基氨基-2-取代嘧啶-4(3H)-酮 3a-d。3a-d 与氧氯化磷反应得到 6-氯呋喃并[2,3-d]色烯基嘧啶胺 4a-d，4a-d 与仲胺反应得到呋喃并[2,3-d]色烯基氨基-2,6-二取代嘧啶-4(3H)-酮 5a-d。此外，5a-d 与 3-氯-2,4-戊二酮反应得到 3-氯呋喃并[2,3-d]色烯基嘧啶并嘧啶 6a-d。后者与哌嗪和吗啉反应得到 1-(呋喃并[2,3-d]色烯基)-嘧啶并嘧啶-3,6,8-三基哌嗪或-3,6,8-三基吗啉 7a-d。新合成化合物的化学结构通过 IR、1H-NMR、13C-NMR 和质谱分析进行了表征。这些化合物还进行了镇痛和抗炎活性筛选。其中一些，特别是 3-7，表现出有希望的活性。
