DOI QR코드

DOI QR Code

Synthesis and Some Properties of 4'-Phenyl-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues

  • Liu, Lian Jin (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Kim, Eun-Ae (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
  • Received : 2011.01.18
  • Accepted : 2011.02.21
  • Published : 2011.05.20

Abstract

Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-substituent with antiviral enhancement, novel 4'-phenyl-5'-norcarbocyclic adenosine phosphonic acid analogues were racemically synthesized via de novo acyclic stereoselective route from propionaldehyde 5. The phenyl substituted cyclopentenols 15a and 15b as key intermediates were successfully constructed via reiterative carbonyl addition of Grignard reagents and ring-closing metathesis of corresponding divinyl 14. The synthesized nucleoside phosphonic acids analogues 19, 20, 21, and 23 were subjected to antiviral screening against HIV-1.

Keywords

References

  1. Maag, H.; Nelson, J. T.; Steiner, J. L.; Prisbe, E. J. J. Med. Chem. 1994, 37, 431. https://doi.org/10.1021/jm00030a001
  2. Haraguchi, K.; Takeda, S.; Tanaka, H.; Nitanda, T.; Baba, M.; Dutschman, G. E.; Cheng, Y.-C. Bioorg. Med. Chem. Lett. 2003, 13, 3775. https://doi.org/10.1016/j.bmcl.2003.07.009
  3. Kumamoto, H.; Nakai, T.; Haraguchi, K.; Nakamura, K. T.; Tanaka, H.; Baba, M.; Cheng, Y.-C. J. Med. Chem. 2006, 49, 7861. https://doi.org/10.1021/jm060980j
  4. Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.; Shigeta, S.; Matuda, A. J. Med. Chem. 1999, 42, 2901. https://doi.org/10.1021/jm990050i
  5. Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385. https://doi.org/10.1016/S0960-894X(99)00010-4
  6. 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
  7. 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
  8. 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
  9. 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
  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. 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
  13. Heapy, A. M.; Bramble, M. A. Tetrahedron 2010, 66, 5424. https://doi.org/10.1016/j.tet.2010.05.027
  14. Corey, E. J.; Kim, C. U. J. Am. Chem. Soc. 1972, 94, 7586. https://doi.org/10.1021/ja00776a056
  15. Corey, E. J.; Cho, H.; Rücker, C.; Hua, D. H. Tetrahedron Lett. 1981, 22, 3455. https://doi.org/10.1016/S0040-4039(01)81930-4
  16. Habrant, D.; Stewart, A. J. W.; Koskinen, A. M. P. Tetrahedron 2009, 65, 7927. https://doi.org/10.1016/j.tet.2009.07.070
  17. Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235. https://doi.org/10.1177/095632020401500502
  18. Amblard, F.; Nolan, S. P.; Agrofoglio, L. A. Tetrahedron 2005, 61, 7067. https://doi.org/10.1016/j.tet.2005.04.040
  19. Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Pavan Kumar, K. V. P. Chem. Rev. 2009, 109, 2551. https://doi.org/10.1021/cr800278z
  20. 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
  21. Li, H.; Yoo, J. C.; Baik, Y. C.; Lee, W.; Hong, J. H. Bull. Korean Chem. Soc. 2010, 31, 2514. https://doi.org/10.5012/bkcs.2010.31.9.2514
  22. Phillion, D. P.; Andrew, S. S. Tetrahedron Lett. 1986, 27, 1477. https://doi.org/10.1016/S0040-4039(00)84289-6
  23. Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697. https://doi.org/10.1021/jo9608275
  24. Hockova, D.; Holy, A.; Masojidkova, 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
  25. 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
  26. Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621. https://doi.org/10.1021/ja00210a064
  27. Lian, L. J.; Yoo, J. C.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2009, 28, 150. https://doi.org/10.1080/15257770902736434

Cited by

  1. ChemInform Abstract: Synthesis and Some Properties of 4′-Phenyl-5′-norcarbocyclic Adenosine Phosphonic Acid Analogues. vol.42, pp.43, 2011, https://doi.org/10.1002/chin.201143191
  2. Recent advances in the synthesis of cyclic 5′-nornucleoside phosphonate analogues vol.463, pp.None, 2018, https://doi.org/10.1016/j.carres.2018.04.009