Asymmetric Synthesis of Novel Thioiso Dideoxynucleosides with Exocyclic Methylene as Potential Antiviral Agents

Journal of Organic Chemistry

Volumn 69, Issue 9, 2004, Pages 3208-3211

  Gunaga, Prashantha ^a   Baba, Masanori ^b   Jeong, Lak Shin ^a  

^a Ewha Womans University   (South Korea)

^b KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TEMPERATURE CONTROL;

CYCLIZATION; PURINE NUCLEOSIDES;

ORGANIC COMPOUNDS;

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; PALLADIUM; THIOISODIDEOXYNUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CYCLIZATION; GLYCOSYLATION; MITSUNOBU REACTION; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

ANTIVIRAL AGENTS; CATALYSIS; CYCLIZATION; DIDEOXYNUCLEOSIDES; GLYCOSYLATION; HYDROCARBONS; METHANE; PALLADIUM; PURINES; PYRIMIDINES; SOLVENTS; TEMPERATURE; THIONUCLEOTIDES; XYLOSE;

EID: 2142708627     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035735b     Document Type: Article

References (17)

1. Jeong, L. S.; Schinazi, R. F.; Beach, J. W.; Kim, H. O.; Nampalli, S.; Shanmuganathan, K.; Alves, A. J.; McMillan, A.; Chu, C. K. J. Med. Chem. 1993, 36, 181 and references therein.
2. ,Calvez, V.; Tubiana, R.; Ghosn, J.; Wirden, M.; Marcelin, A. G.; Westling, C.; Shoen, H.; Harmenberg, J.; Mardh, G.; Oberg, B.; Katlama, C. Antiviral Ther. 2002, S5, 7.
3. (a) Kim, H. O.; Schinazi, R. F.; Shanmuganathan, K.; Jeong, L. S.; Beach, J. W.; Nampalli, N.; Cannon, D. L.; Chu, C. K. J. Med. Chem. 1993, 36, 519.
4. (b) Giles, F. J.: Garcia-Manero, G.; Cortes, J. E.; Baker, S. D.; Miller, C. B.; O'Brien, S. M.; Thomas, D. A.; Andreeff, M.; Bivins, C.; Jolivet, J.; Kantarjian, H. M. J. Clin. Oncol. 2002, 20, 656.
5. (a) Kim, H. O.; Schinazi, R. F.; Nampalli, S.; Shanmuganathan, K.; Cannon, D. L.; Alves, A. J.; Jeong, L. S.; Beach, J. W.; Chu, C. K. J. Med. Chem. 1993, 36, 30.
6. (b) Corbett, A. H.; Rublein, J. C. Curr. Opin. Invest. Drugs 2001, 2, 348.
7. Lai, C. L.; Rosmawati, M.; Lao, J.; Van Vlierberghe, H.; Anderson, F. H. ; Thomas, N.; DeHertogh, D. Gastroenterology 2002, 123, 1831.
8. (a) Jeong, L. S.; Yoo, S. J. Bioorg. Med. Chem. Lett. 1998, 8, 847.
9. (b) Yoo, S. J.; Kim, H. O.; Lim, Y.; Kim, J.; Jeong, L. S. Bioorg. Med. Chem. 2002, 10, 215.
10. (a) Nair, V.; Nueska, Z. M. J. Am. Chem. Soc. 1992, 114, 7951.
11. (b) Huryn, D. M.; Sluboski, B. C.; Tam, S. Y.; Weigele, M.; Sim, I.; Anderson, B. D.; Mitsuya, H.; Broder, S. J. Med. Chem. 1992, 35, 2347.
12. (a) Yoshimura, Y.; Kitano, K.; Yamada, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem. 1997, 62, 3140.
13. (b) Jeong, L. S.; Moon, H. R.; Choi, Y. J.; Chun, M. W.; Kim, H. O. J. Org. Chem. 1998, 63, 4821.
14. Ma, T.; Pai, S. B.; Zhu, Y. L.; Lin, J. S.; Shanmuganathan, K.; Du, J.; Wang, C.; Kim, H.; Newton, M. G.; Cheng, Y. C.; Chu, C. K. J. Med. Chem. 1996, 39, 2835.
15. (a) Mitsunobu, O. Synthesis 1981, 1.
16. (b) Jenny, T. F.; Horlacher, J.; Previsani, N.; Benner, S. A. Helv. Chim. Acta 1992, 75, 1944.
17. Bannal, C.; Chavis, C.; Lucas, M. J. Chem. Soc., Perkin Trans. 1 1994, 1401.