Synthesis, Antiaggregant, and Antioxidant Activity of 2-{[1-iso-butyl-3-methyl-7-(thietanyl-3)xanthin-8-yl]thio}acetic Acid Salts

• Published in: Pharmaceutical chemistry journal Vol. 54; no. 9; pp. 891 - 896
• Main Authors: Khaliullin, F. A., Mamatov, Zh. K., Timirkhanova, G. A., Samorodov, A. V., Bashirova, L. I.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-12-2020; Springer
• Subjects: Acetic acid; Antioxidants; Aspirin; Medicine; Organic acids; Organic Chemistry; Pharmacology/Toxicology; Pharmacy; Search for New Drugs; antiaggregant activity; thietanes; xanthines; antioxidant activity
• DOI: 10.1007/s11094-020-02293-w
• EISSN: 1573-9031
• ISSN: 0091-150X

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.