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Synthesis, Antiaggregant, and Antioxidant Activity of 2-{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic Acid Salts
Pharmaceutical Chemistry Journal ( IF 0.8 ) Pub Date : 2020-12-01 , DOI: 10.1007/s11094-020-02293-w
F. A. Khaliullin , Zh. K. Mamatov , G. A. Timirkhanova , A. V. Samorodov , L. I. Bashirova

8-Bromo-1-iso-butyl-3-methyl-7-(thietanyl-3)xanthine (II) was synthesized by alkylation of 8-bromo-3-methyl-7-(thietanyl-3)xanthine (I) with isobutyl bromide. Nucleophilic substitution of II with thioglycolic acid gave 2{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic acid (III). A series of water-soluble salts of 2{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic acid (IVa-h) were synthesized by reaction of III with organic and inorganic bases. Compounds possessing antiaggregant activity on the level of acetylsalicylic acid were found among salts IV. All obtained compounds except for IVa and IVc suppressed lipid peroxidation less than ascorbic acid. However, all synthesized compounds suppressed generation of reactive oxygen species by phagocytes, in contrast to ascorbic acid.

中文翻译:

2-{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}乙酸盐的合成、抗聚集剂和抗氧化活性

8-Bromo-1-iso-butyl-3-methyl-7-(thietanyl-3)xanthine (II) 是通过 8-bromo-3-methyl-7-(thietanyl-3)xanthine (I) 与异丁基溴。II与巯基乙酸的亲核取代得到2{[1-异丁基-3-甲基-7-(thietanyl-3)xanthin-8-yl]硫代}乙酸(III)。2{[1-异丁基-3-甲基-7-(thietanyl-3)xanthin-8-yl]thio}乙酸(IVa-h)的一系列水溶性盐由III与有机碱和无机碱。在盐IV中发现了在乙酰水杨酸水平上具有抗聚集活性的化合物。除了IVa和IVc之外,所有获得的化合物对脂质过氧化的抑制都小于抗坏血酸。然而,与抗坏血酸相反,所有合成的化合物都抑制吞噬细胞产生活性氧。
更新日期:2020-12-01
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