SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 10: 2205 - 2211

DOI: https://doi.org/10.6023/cjoc201504036

Notes

Synthesis of 6-Alkylamino-2-ethylthiopurine Nucleoside Compounds and Their Antiplatelet Aggregation Activities

  • Wang Zijian ,
  • Li Shunlai ,
  • Yu Mingwu ,
  • Luo Yuan ,
  • Wang Shuai ,
  • Wang Yongan ,
  • Du Hongguang
Expand
  • a Beijing University of Chemical Technology, Beijing 100029;
    b Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences, State Key Laboratory ofToxicology and Medical Countermeasures, Beijing 100850

Received date: 2015-04-23

  Revised date: 2015-06-04

  Online published: 2015-06-12

Supported by

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

Fold

Abstract

Guanosine (1) as the starting material, reacted with acetic anhydride to obtain 2',3',5'-tri-O-acetyl-guanosine (2), which reacted with TsCl to obtain 2-amino-6-tosyl-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-ethylthio-6-tosyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine (4). Finally, compounds 5 were acquired by aminolysis and deprotection of 4. Ten new compounds were synthesized and all compounds were characterized with 1H NMR, 13C NMR, IR and HRMS. Meanwhile, their antiplatelet aggregation rate was measured. The results show that these compounds have a certain antiplatelet aggregation activity.

Key words： purine derivatives; synthesis; structure characterization; antiplatelet aggregation activity

Cite this article

Wang Zijian , Li Shunlai , Yu Mingwu , Luo Yuan , Wang Shuai , Wang Yongan , Du Hongguang . Synthesis of 6-Alkylamino-2-ethylthiopurine Nucleoside Compounds and Their Antiplatelet Aggregation Activities[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2205 -2211 . DOI: 10.6023/cjoc201504036

References

[1] Pravin, P.; Abhay, N.; Krishnachaya, G. A. J. Org. Chem. 2014, 79(5), 2331.
[2] Siyang, H. X.; Wu, X. R.; Liu, H. L.; Wu, X. Y.; Liu, P. N. J. Org. Chem. 2014, 79(3), 1505.
[3] Xia, R.; Xie, M. S.; Niu, H. Y.; Qu, G. R.; Guo, H. M. Org. Lett. 2014, 16(2), 444.
[4] Giulia, V.; Martina, M.; Deborah, S.; Emmanuele, C.; Miroslava, K.; Giovanni, M.; Silvia, A.; Marco, R.; Maurizio, B. ACS Comb. Sci. 2014, 16(4), 168.
[5] Katrin, M.; Klaus, R. Ach. Pharm. Chem. Life Sci. 2006, 339, 115.
[6] Wang, T.; Du, H. G. Chin. J. Org. Chem. 2012, 32, 1720 (in Chinese). (汪韬, 杜洪光, 有机化学, 2012, 32, 1720.)
[7] He, Q. W.; Du, H. G. Chin. J. Org. Chem. 2012, 32, 1678 (in Chinese). (何琦文, 杜洪光, 有机化学, 2012, 32, 1678.)
[8] Deng, C. E.; Li, S. L.; Liu, X W.; Du, H. G. Chin. J. Org. Chem. 2013, 33, 1741 (in Chinese). (邓聪迩, 李顺来, 刘祥伟, 杜洪光, 有机化学, 2013, 33, 1741.)
[9] Liu, G. C.; Xu, J. X.; Park, K. C.; Chen, N.; Zhang, S.; Ding, Z. R.; Wang, F.; Du, H. G. Tetrahedron 2011, 67, 5156.
[10] Wu, Z. J.; Li, S. L.; Ding, Z. R.; Du, H. G. Chin. J. Org. Chem. 2011, 31, 1618 (in Chinese). (吴兆军, 李顺来, 丁忠仁, 杜洪光, 有机化学, 2011, 31, 1618.)

Options
Outlines

/

〈 〉