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.
Highlights
Khellin and visnagen, 4,9-dimethoxy- or 4-methoxy-7-methyl-furo[3,2-g]chromen-5-one, respectively (Figure 1) are obtained from fruits and seeds of the plant Ammi visnaga
The khellin and visnagen extract has been widely employed as a herbal medicine in the treatment of angina [1]
Khellin is used as a spasmolytic agent and for kidney stone treatment [2]
Summary
4,9-dimethoxy- or 4-methoxy-7-methyl-furo[3,2-g]chromen-5-one, respectively (Figure 1) are obtained from fruits and seeds of the plant Ammi visnaga. The khellin and visnagen extract has been widely employed as a herbal medicine in the treatment of angina [1]. Khellin is used as a spasmolytic agent and for kidney stone treatment [2]. Khellin and visnagen extract significantly prolongs the induction time of nucleation of calcium oxalate [3]. Khellin has been used for photochemotherapeutic treatment of vitiligo and psoriasis [4] and the photodynamic properties of khellin and visnagen in their photoreaction with DNA have been studied [5]. Khellin was proved to have phototherapeutic properties that are similar to those of the psoralens, but with substantially lower phototoxic effects and DNA mutation effects. Subsequent activation of khellin with UV light stimulates the melanocytes in the hair follicles [6]. The fact that furochromone derivatives are known to have anti-inflammatory properties [7] and analgesic properties [8], prompted us to synthesize and investigate such properties in khellin and visnagen derivatives as typical furochromones
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