DOI QR코드

DOI QR Code

Synthesis and Anti-HIV Activity of Novel 4'-Ethyl-5'-norcarbocyclic Adenosine Phosphonic Acid Analogues

  • Yoo, Jin-Cheol (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Li, Hua (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Lee, Won-Jae (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
  • 투고 : 2010.07.20
  • 심사 : 2010.09.15
  • 발행 : 2010.11.20

초록

Novel 4'-ethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were synthesized from propionaldehyde 5 through a de novo acyclic synthetic route using reiterative Grignard additions and ring-closing metathesis (RCM) as key reactions. The synthesized nucleoside phosphonic acids analogues 17, 18, 19, and 21 were subjected to antiviral screening against human immunodeficiency virus.

키워드

참고문헌

  1. Maag, H.; Rydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D.; Verheyden, J. P.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440. https://doi.org/10.1021/jm00086a013
  2. Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385. https://doi.org/10.1016/S0960-894X(99)00010-4
  3. Boojamra, C. G.; Parrish, J. P.; Sperandio, D.; Gao, Y.; Petrakovsky, O. V.; Lee, S. K.; Markevich, D. Y.; Vela, J. E.; Laflamme, G.; Chen, J. M.; Ray, A. S.; Barron, A. C.; Sparacino, M. L.; Desai, M. C.; Kim, C. U.; Cihlar, T.; Mackman, R. L. Bioorg. Med. Chem. 2009, 17, 1739. https://doi.org/10.1016/j.bmc.2008.12.028
  4. Mackman, R. L.; Boojamra, C. G.; Prasad, V.; Zhang, L.; Lin, K. Y.; Petrakovsky, O.; Babusis, D.; Chen, J.; Douglas, J.; Grant, D.; Hui, H. C.; Kim, C. U.; Markevitch, D. Y.; Vela, J.; Ray, A.; Cihlar, T. Bioorg. Med. Chem. Lett. 2007, 17, 6785 https://doi.org/10.1016/j.bmcl.2007.10.038
  5. Ray, A. S.; Vela, J. E.; Boojamra, C. G.; Zhang, L.; Hui, H.; Callebaut, C.; Stray, K.; Lin, K. Y.; Gao, Y.; Mackman, R. L.; Cihlar, T. Antimicrob. Agents Chemother. 2008, 52, 648. https://doi.org/10.1128/AAC.01209-07
  6. Ray, A. S.; Vela, J. E.; Boojamra, C. G.; Zhang, L.; Hui, H.; Callebaut, C.; Stray, K.; Lin, K. Y.; Gao, Y.; Mackman, R. L.; Cihlar, T. Antimicrob. Agents Chemother. 2008, 52, 648. https://doi.org/10.1128/AAC.01209-07
  7. Boojamra, C. G.; Mackman, R. L.; Markevitch, D. Y.; Prasad, V.; Ray, A. S.; Douglas, J.; Grant, D.; Kim, C. U.; Cihlar, T. Bioorg. Med. Chem. Lett. 2008, 18, 1120. https://doi.org/10.1016/j.bmcl.2007.11.125
  8. Mackman, R. L.; Lin, K. Y.; Boojamra, C. G.; Hui, H.; Douglas, J.; Grant, D.; Petrakovsky, O.; Prasad, V.; Ray, A. S.; Cihlar, T. Bioorg. Med. Chem. Lett. 2008, 18, 1116. https://doi.org/10.1016/j.bmcl.2007.11.126
  9. Kim, C. U.; Luh, B. Y.; Misco, P. F.; Bronson, J. J.; Hitchcock, M. J.; Ghazzouli, I.; Martin, J. C. J. Med. Chem. 1990, 33, 1207. https://doi.org/10.1021/jm00166a019
  10. Wu, T.; Froeyen, M.; Kempeneers, V.; Pannecouque, C.; Wang, J.; Busson, R.; De Clercq, E.; Herdewijn, P. J. Am. Chem. Soc. 2005, 127, 5056. https://doi.org/10.1021/ja043045z
  11. Kim, C. U.; Luh, B. Y.; Martin, J. C. J. Org. Chem. 1991, 56, 2642. https://doi.org/10.1021/jo00008a013
  12. Stoeckler, J. D.; Cambor, C.; Parks, R. E., Jr. Biochemistry 1980, 19, 102. https://doi.org/10.1021/bi00542a016
  13. Heapy, A. M.; Bramble, M. A. Tetrahedron 2010, 66, 5424. https://doi.org/10.1016/j.tet.2010.05.027
  14. Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
  15. Amblard, F.; Nolan, S. P.; Agrofoglio, L. A. Tetrahedron 2005, 61, 7067. https://doi.org/10.1016/j.tet.2005.04.040
  16. Liu, L. J.; Kim, S. W.; Lee, W.; Hong, J. H. Bull. Korean Chem. Soc. 2009, 30, 2989 https://doi.org/10.5012/bkcs.2009.30.12.2989
  17. Li, H.; Kim, S. W.; Hong, J. H. Bull. Korean Chem. Soc. 2010, 31, 2180. https://doi.org/10.5012/bkcs.2010.31.8.2180
  18. Oh, H. S.; Kang, H. Y. Tetrahedron 2010, 66, 4307. https://doi.org/10.1016/j.tet.2010.04.039
  19. Phillion, D. P.; Andrew, S. S. Tetrahedron Lett. 1986, 27, 1477. https://doi.org/10.1016/S0040-4039(00)84289-6
  20. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697. https://doi.org/10.1021/jo9608275
  21. Hocková, D.; Holý, A.; Masojídková, M.; Keough, D. T.; De Jersey, J.; Guddat, L. W. Bioorg. Med. Chem. 2009, 17, 6218. https://doi.org/10.1016/j.bmc.2009.07.044
  22. Koh, Y. H.; Shim, J. H.; Wu, J. Z.; Zhong, W.; Hong, Z.; Girardet, J. L. J. Med. Chem. 2005, 48, 2867. https://doi.org/10.1021/jm049029u
  23. Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621. https://doi.org/10.1021/ja00210a064
  24. Lian, L. J.; Yoo, J. C.; Hong, J. H. Nucleos. Nucleot. Nucl. 2009, 28, 150. https://doi.org/10.1080/15257770902736434

피인용 문헌

  1. ChemInform Abstract: Synthesis and anti-HIV Activity of Novel 4′-Ethyl-5′-norcarbocyclic Adenosine Phosphonic Acid Analogues. vol.42, pp.13, 2011, https://doi.org/10.1002/chin.201113208
  2. 5′-Norcarbocyclic nucleoside analogs vol.63, pp.5, 2014, https://doi.org/10.1007/s11172-014-0551-5
  3. The chemistry of the carbon–transition metal double and triple bond: Annual survey covering the year 2010 vol.256, pp.13, 2010, https://doi.org/10.1016/j.ccr.2012.02.015