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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1720 - 1727

DOI: https://doi.org/10.6023/cjoc201303018

Articles

Synthesis of 6-Alkylamino-2-alkylthio-9-(2-hydroxyethyl)-8-methoxy-purines and Their Anti-platelet Aggregation Activities

  • Wang Tao ,
  • Du Hongguang
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  • College of Science, Beijing University of Chemical Technology, Beijing 100029

Received date: 2013-03-12

  Revised date: 2013-04-11

  Online published: 2013-04-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272022).

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Abstract

2-Amino-6-chloropurine (1) was reacted with 2-bromoethyl acetate to yield 9-acetoxyethyl-2-amino-6-chloro-purine (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.

Key words： purine derivatives; synthesis; characterization; anti-platelet aggregation

Cite this article

Wang Tao , Du Hongguang . Synthesis of 6-Alkylamino-2-alkylthio-9-(2-hydroxyethyl)-8-methoxy-purines and Their Anti-platelet Aggregation Activities[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1720 -1727 . DOI: 10.6023/cjoc201303018

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