Synthesis and hypnotic activities of 4-thio analogues of N3-substituted uridines |
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Authors: | Kozai S Maruyama T Kimura T Yamamoto I |
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Institution: | Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan. |
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Abstract: | Reaction of tri-O-acetyluridine (1) with benzyl bromide or 2-chloroacetophenone in the presence of K2CO3 gave the N3-substituted analogues 2a,c. Condensation of 1 with (+/-)-1-phenylethanol or 3,5-dimethylbenzyl alcohol using the Mitsunobu reaction also gave 2b,d in good yields. These compounds were allowed to react with Lawesson's reagent and were subsequently treated with ammonia to afford the 4-thiouracil derivatives 5a-d. Compounds 5a-c showed moderate hypnotic activity in mice. However, N3-(3,5-dimethyl)benzyl derivatives 3d, 5d were found to be almost inactive in this assay. |
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