2-Amino-6-chloropurine (1) as the starting material was treated with 2-bromoethyl acetate to yield 9-acetoxyethyl-2-amino-6-chloropurine (2). Compound 2 was diazotized and reacted with disulfides to afford 9-acetoxyethyl-2-alkythio-6-chloropurine (3). 9-Acetoxyethyl-6-alkylamino-2-alkylthio purines (4) were acquired by aminolysis reaction of compounds 3. Their structures were determined by IR, 1 H NMR,
13C NMR and HRMS techniques. Meanwhile, the anti-platelet aggregation rates of compounds 4 were measured.
2-Amino-6-chloropurine (1) was reacted with 2-bromoethyl acetate to yield 9-acetoxyethyl-2-amino-6-chloropurine (2), which was treated with NBS to afford 9-acetoxyethyl-2-amino-8-bromo-6-chloropurine (3). 3 was reacted with sodium methanol to afford 2-amino-6-chloro-9-(2-hydroxyethyl)-8-methoxypurine (4), and then 4 was treated with acetic anhydride to yield 9-acetoxyethyl-2-amino-6-chloro-8-methoxypurine (5). After that 5 was diazotized and reacted with dialkyl disulfide to yield 9-acetoxyethyl-2-alkylthio-6-chloro-8-methoxypurine (6) and 6 was treated with amine to afford 9-acetoxyethyl-6-alkylamino-2-alkylthio-8-methoxypurine (7). Deprotection of hydroxyl group in compound 7 provided target compound 8. All 24 novel compounds 3~8 were acquired and their structures were identified by 1H NMR, 13C NMR, IR and HRMS techniques. Besides, the anti-platelet aggregation activities of the nine target compounds were tested.
Guanosine (1) as the starting material, reacted with acetic anhydride to obtain 2',3',5'-triO -acetyl-guanosine (2), which reacted with TsCl to obtain 2-amino-6-tosyl-9-(2',3',5'-triO -acetyl-β-D-ribofuranosyl)purine (3). Compound 3 was diazotized with isoamyl nitrite and then reacted with dialkyl disulfides to afford 2-ethylthio-6-tosyl-9-(2',3',5'-triO -acetyl-β-Dribofuranosyl)purine (4). Finally, compounds 5 were acquired by aminolysis and deprotection of 4. Ten new compounds were synthesized and all compounds were characterized with 1 H NMR, 13 C NMR, IR and HRMS. Meanwhile, their antiplatelet aggregation rate was measured. The results show that these compounds have a certain antiplatelet aggregation activity.
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