DOI QR코드

DOI QR Code

Synthesis and Antiviral Activity of Novel 4'-Branched Carbocyclic C-Nucleoside

  • 발행 : 2005.09.20

초록

The first synthesis of a 4'-branched carbocyclic C-nucleoside 11 was achieved via the key intermediate 6, which was prepared using Knovenagel type condensation from ketone derivative 4.

키워드

참고문헌

  1. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A. Tetrahedron 1994, 50, 10611-10670 https://doi.org/10.1016/S0040-4020(01)89258-9
  2. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571 https://doi.org/10.1016/S0040-4020(01)88122-9
  3. Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; St Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082
  4. Watanabe, K. A. In Chemistry of Nucleosides & Nucleotides; Townsend, l. B., Ed.; Plenum: New York, 1994; Vol. 3, Chapter 5
  5. Shaban, M. A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1997, 68, 223 https://doi.org/10.1016/S0065-2725(08)60363-3
  6. Liang, C.; Ma, T.; Cooperwood, J. S.; Du, J.; Chu, C. K. Carbohydr. Res. 1997, 303, 33 https://doi.org/10.1016/S0008-6215(97)00143-2
  7. Chu, C. K.; Zuckerman, L. B.; Sato, S.; Crabtree, G. W.; Bogden, A. E.; Lim, M. I.; Klein, R. S. Biochem. Pharmacol. 1984, 33, 1229 https://doi.org/10.1016/0006-2952(84)90174-6
  8. Zimmerman, T. P.; Deeprose, R. D.; Wolberg, G.; Stopford, C. R.; Duncan, G. S.; Miller, W. H.; Miller, R. L.; Lim, M. I.; Ren, W. Y.; Klein, S. Biochem. Pharmacol. 1983, 32, 1211 https://doi.org/10.1016/0006-2952(83)90274-5
  9. Buchanan, J. G. Fortschr. Chem. Org. Naturst. 1983, 44, 243
  10. Buchenal, J. H.; Ciovacco, K.; Kalaher, K.; O'Toole, T.; Kiefner, R.; Dowing, M. D.; Chu, C. K.; Watanabe, K. A.; Wempen, I.; Fox, J. J. Cancer Res. 1976, 36, 15
  11. Fuertes, M.; Garcia-Lopez, T.; Garcia-Munoz, E.; Stud, M. J. Org. Chem. 1976, 41, 4074 https://doi.org/10.1021/jo00888a005
  12. Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. C.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. J. Med. Chem. 1977, 20, 256 https://doi.org/10.1021/jm00212a014
  13. Ueland, P. M. Pharmacol. Rev. 1982, 34, 223
  14. Palmer, J. L.; Abeles, R. H. J. Biol. Chem. 1979, 254, 1217
  15. Fissekis, J. D.; Market Creegan, B. J. Org. Chem. 1967, 32, 3595 https://doi.org/10.1021/jo01286a066
  16. Katagiri, N.; Haneda, T.; Kaneko, C. Chem. Pharm. Bull. 1986, 34, 4875 https://doi.org/10.1248/cpb.34.4875
  17. Katagiri, N.; Haneda, T.; Hayasaka, E.; Watanabe, N.; Kaneko, C. J. Org. Chem. 1988, 53, 226 https://doi.org/10.1021/jo00236a057
  18. Katagiri, N.; Nomura, M.; Kaneko, C. Heterocycles 1990, 30, 211 https://doi.org/10.3987/COM-89-S5
  19. Katagiri, N.; Tomura, M.; Haneda, T.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1987, 1422
  20. Coockson, R. C.; Dufield, P. J.; Scopes, D. I. C. J. Chem. Soc., Perkin Trans. 1 1986, 393 https://doi.org/10.1039/p19860000393
  21. Saksena, A. K.; Ganguly, A. K. Tetrahedron 1982, 22, 5227
  22. Takahashi, T.; Kotsubo, H.; Koizumi, T. Tetrahedron: Asymmetry 1991, 2, 1035 https://doi.org/10.1016/S0957-4166(00)86154-6
  23. Zhou, J.; Yang, M.; Schnell, S. W. Tetrahedron Lett. 2004, 45, 8233 https://doi.org/10.1016/j.tetlet.2004.09.007
  24. Ko, O. H.; Hong, J. H. Tetrahedron Lett. 2002, 43, 6399 https://doi.org/10.1016/S0040-4039(02)01384-9
  25. Kim, J. W.; Choi, B. G.; Hong, J. H. Bull. Korean Chem. Soc. 2004, 25, 1812 https://doi.org/10.5012/bkcs.2004.25.12.1812
  26. Kamath, V. P.; Ananth, S.; Bantia, S.; Morris, P. E. J. Med. Chem. 2004, 47, 1 https://doi.org/10.1021/jm030283g

피인용 문헌

  1. First Synthesis and Anti-HIV Evaluation of 4′-Methyl-Cyclopentanyl 9-Deazaadenosine vol.27, pp.10-11, 2008, https://doi.org/10.1080/15257770802341392
  2. -Nucleosides vol.28, pp.4, 2009, https://doi.org/10.1080/15257770902946058
  3. Antioxidant and Antitumor Activities of New Synthesized Aromatic C-Nucleoside Derivatives vol.19, pp.4, 2014, https://doi.org/10.3390/molecules19045163
  4. Activity of 4′-Modified Analogues of ddA as Potent Anti-HIV Agents vol.342, pp.10, 2009, https://doi.org/10.1002/ardp.200900063
  5. Simple Synthesis and Anti-Hiv Activity of Novel 3&vprime;-Vinyl Branched Apiosyl Pyrimidine Nucleosides vol.25, pp.8, 2005, https://doi.org/10.1080/15257770600793869
  6. Synthesis and Antiviral Activity of Novel 4′-Branched Carbocyclic C-Nucleoside. vol.37, pp.7, 2005, https://doi.org/10.1002/chin.200607213
  7. Chemoenzymatic synthesis of novel adenosine carbanucleoside analogues containing a locked 3′-methyl-2′,3′-β-oxirane-fused system vol.63, pp.23, 2007, https://doi.org/10.1016/j.tet.2007.03.122
  8. Synthesis of 2'-fluoro and 2',4'-dimethyl pyrimidine C-nucleoside analogues as potential anti-HCV agents. vol.29, pp.3, 2005, https://doi.org/10.1080/15257771003705617
  9. Nucleosides with Transposed Base or 4′-Hydroxymethyl Moieties and Their Corresponding Oligonucleotides vol.115, pp.24, 2015, https://doi.org/10.1021/acs.chemrev.5b00545