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Synthesis and immunobiological activity of base substituted 2-amino-3-(purin-9-yl)propanoic acid derivatives.
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2005 Apr 1 , DOI: 10.1016/j.bmc.2005.01.054
Petra Doláková , Antonín Holý , Zdeněk Zídek , Milena Masojídková , Eva Kmoníčková

2-Amino-3-(purin-9-yl)propanoic acids substituted at position 6 of the purine base moiety by dimethylamino, cyclopropylamino, pyrrolidin-1-yl, hydroxy, and sulfanyl group as well as their 2-aminopurine analogues were prepared from corresponding 9-(2,2-diethoxyethyl)purines and 2-aminopurines, respectively, by the Strecker synthesis. 2-Aminopropanoic acid derivatives were tested for their immunostimulatory and immunomodulatory potency. Some of these compounds significantly enhanced secretion of chemokines RANTES and MIP-1alpha, the most potent was 2-amino-6-sulfanylpurine derivative. Most of these compounds also augmented NO biosynthesis triggered primarily by IFN-gamma.

中文翻译:

碱取代的2-氨基-3-(嘌呤-9-基)丙酸衍生物的合成和免疫生物学活性。

制备在嘌呤碱基部分的6位被二甲基氨基,环丙基氨基,吡咯烷基-1-基,羟基和硫烷基取代的2-氨基-3-(嘌呤-9-基)丙酸及其2-氨基嘌呤类似物分别通过Strecker合成法从相应的9-(2,2-二乙氧基乙基)嘌呤和2-氨基嘌呤中分离得到。测试了2-氨基丙酸衍生物的免疫刺激和免疫调节能力。这些化合物中的一些显着增强了趋化因子RANTES和MIP-1alpha的分泌,最有效的是2-氨基-6-硫烷基嘌呤衍生物。这些化合物大多数还增强了主要由IFN-γ触发的NO生物合成。
更新日期:2017-01-31
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