新型杂合酮的替代合成方法——功能化次黄嘌呤嘧啶

V. Povstyanoy, T. A. Yuyrova, A. N. Retchitskiy, A. A. Krysko
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引用次数: 0

摘要

已知二氢嘧啶和黄嘌呤的衍生物具有广谱作用的生理活性。在一个分子内的特定杂环片段的组合可以导致其已知生物活性类型的增加以及新的活性类型的发现。我们之前已经报道了由功能化二氢嘧啶组成的中间体的合成,这些中间体通过亚甲基桥与茶碱、3-甲基黄嘌呤和咪唑的卤素取代衍生物连接。还观察到这些化合物会与N -亲核试剂反应,形成各种支链和环状产物。本工作的目的是确定溴甲基二氢嘧啶和次黄嘌呤在C6和C1位置通过亚甲基桥联得到杂环产物的最佳条件。值得注意的是,在利用Biginelli反应合成二氢嘧啶核的过程中,后者可以使用结构多样的芳香醛进行广泛修饰,这解释了反应产物的结构多样性。在尝试了各种反应条件后,我们得出了获得产品的最佳方法是将溴甲基取代二氢嘧啶和1-钾- 2-氯- 7-甲基次黄嘌呤在干乙醇中保持等摩尔比4小时。二氢嘧啶环C5处的酯基和次黄嘌呤片段C2处的氯离去基使得这些结构可以被认为是进一步合成缩合嘧啶和黄嘌呤体系的前缺失合子。通过HPLC/MS、1H、13C NMR等方法对新化合物的结构进行了确证。
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ALTERNATIVE METHODS OF SYNTHESIS OF NOVEL HETEROSYNTHONES – FUNCTIONALIZED HYPOXANTHINE PYRIMIDINES
It has been known that derivatives of dihydropyrimidine and xanthine possess the physiological activity of the wide spectrum of action. The combination of the specified heterocyclic fragments within one molecule can lead to the increase of its known types of biological activity as well as to the discovery of novel types of activity. We have previously reported the synthesis of intermediates, which consist of functionalized dihydropyrimidines, connected via a methylene bridge with the halogen substituted derivatives of the ophylline, 3-methylxanthine and imidazole. It was also observed that these compounds would react with N‑nucleophiles with the formation of various branched and cyclic products. The aim of this work was to determine the optimal conditions for obtaining heterocyclic products as a result of conjugation of bromomethyldihydropyrimidine and hypoxanthine at the positions C6 and C1 via a methylene bridge. It is important to note, that the latter can be widely modified by using structurally diverse aromatic aldehydes during the synthesis of dihydropyrimidine core by using Biginelli reaction, which explains structural diversity of the reaction products. After having tried various reaction conditions, we have concluded that the optimal method for obtaining the products entailed keeping equimolar ratios of bromomethyl substituted dihydropyrimidines and 1-potassium‑2-chloro‑7-methylhypoxanthine in dry ethanol for 4 hours. The ester group at the C5 of dihydropyrimidine ring and a chlorine leaving group at C2 of hypoxanthine fragments of the molecule allow to consider these structures as pro missing synthons for farther synthesis of condensed pyrimidine and xanthine systems. The structures of novel compounds have been confirmed with the methods such as HPLC/MS, 1H, and 13C NMR spectroscopy.
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