Synthesis of 6-Amino-2-alkylthio Adenosine and Their Anti-platelet Aggregation Activity

doi:10.7503/cjcu20130198

Abstract

Abstract:

Some purine derivatives are effective inhibitors of platelet aggregation. Guanosine(1), as the starting material, was protected by acetic anhydride to get 2',3',5' -tri-O-acetyl-guanosine(2), then chlorinated with phosphorus oxychloride to obtain 2-amino-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine(3). Compound 3 was diazotized with isoamyl nitrite and then reacted with dialkyl disulfides to afford 2-alkyl(aryl)thio-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purines(4a-4d). 6-Amino-2-alkylthio adenosine(5a-5l) were acquired by aminolysis and deprotection reaction of compounds 4a-4d. The structures of the compounds were identified by ¹H NMR, ¹³C NMR, IR and high resolution mass spectrometer(HRMS). In addition, the platelet aggregation rates(PAR) for the final compounds were measured. The results show that these compounds have a certain anti-platelet aggregation activity under 10 μmol/L. 6-(3-Phenyl propyl)azyl-2-propylthio adenosine has the most significant activity, the PAR was up to 9.8%.

Key words: Purine derivative, Anti-platelet aggregation, Structural characterization

CLC Number:

O621.3

TrendMD:

WEI Yong-Ji, LI Shun-Lai, YU Ming-Wu, DU Hong-Guang. Synthesis of 6-Amino-2-alkylthio Adenosine and Their Anti-platelet Aggregation Activity[J]. Chem. J. Chinese Universities, 2013, 34(11): 2524.

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