Design and racemic synthesis of conformationally restricted carbocyclic pyrimidine nucleoside analogs based on the structure of the L-nucleoside residue in heterochiral DNA

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 3, 1998, Pages 458-461

  Urata, Hidehito ^a   Miyagoshi, Hidetaka ^a   Kakuya, Hitoshi ^a   Tokumoto, Hideki ^a   Kawahata, Takuya ^b   Otake, Toru ^b   Akagi, Masao ^a  

^a OSAKA MEDICAL COLLEGE   (Japan)

^b OSAKA PREFECTURAL INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

Carbocyclic nucleoside; O cyclonucleoside; Restricted glycosidic conformation

Indexed keywords

2 AMINO 5AALPHA,7ALPHA,8BETA,8AALPHA TETRAHYDRO 7 HYDROXY 8 HYDROXYMETHYL 4H,6H CYCLOPENT[4,5]OXAZOLO[3,2 C]PYRIMIDIN 4 ONE; 5AALPHA,7ALPHA,8BETA,8AALPHA TETRAHYDRO 7 HYDROXY 8 HYDROXYMETHYL 2H,6H CYCLOPENT[4,5]OXAZOLO[3,2 C]PYRIMIDINE 2,4(3H) DIONE; CARBOCYCLIC 6,6',2 CYCLO 2' DEOXYCYTIDINE; CARBOCYCLIC 6,6',2 CYCLO 2' DEOXYURIDINE; PYRIMIDINE NUCLEOSIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CONTROLLED STUDY; CYCLIZATION; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; RACEMIC MIXTURE; VIRUS INHIBITION;

EID: 0031969416     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.458     Document Type: Article

References (28)

1. Mitsuya H., Yarchoan R., Broder S., Science, 249, 1533-1544 (1990).
2. Soudeyns H., Yao X.-J., Gao Q., Belleau B., Kraus J.-L., Nguyen-Ba N., Spira B., Wainberg M. A., Antimicrob. Agents Chemother., 35, 1386-1390 (1991).
3. Coates J. A. V., Cammack N., Jenkinson H. J., Mutton I. M., Pearson B. A., Storer R., Cameron J. M., Penn C. R., Antimicrob. Agents Chemother., 36, 202-205 (1992).
4. Schinazi R. F., Chu C. K., Peck A., McMillan A., Mathis R., Cannon D., Jeong L.-S., Beach J. W., Choi W.-B., Yeola S., Liotta D. C., Antimicrob. Agents Chemother., 36, 672-676 (1992).
5. Furman P. A., Wilson J. E., Reardon J. E., Painter G. R., Antiviral Chem. Chemother., 6, 345-355 (1995).
6. Garbesi A., Capobianco M. L., Colonna F. P., Tondelli L., Arcamone F., Manzini G., Hilbers C. W., Aelen J. M. E., Blommers M. J. J., Nucleic Acids Res., 21, 4159-4165 (1993).
7. Urata H., Ogura E., Shinohara K., Ueda Y., Akagi M., Nucleic Acids Res., 20, 3325-3332 (1992).
8. Urata H., Ueda Y., Suhara H., Nishioka E., Akagi M., J. Am. Chem. Soc., 115, 9852-9853 (1993).
9. Urata H., Akagi M., Tetrahedron Lett., 37, 5551-5554 (1996).
10. a) Dickerson R. E., Drew H. R., J. Mol. Biol., 149, 761-786 (1981):
11. b) Drew H. R., Wing R. M., Takano T., Broka C., Tanaka S., Itakura K., Dickerson R. E., Proc. Natl. Acad. Sci. U.S.A., 78, 2179-2183 (1981).
12. a) Miller N., Fox J. J., J. Org. Chem., 29, 1772-1776 (1964);
13. b) Falco E. A., Otter B. A., Fox J. J., ibid., 35, 2326-2330 (1970);
14. c) Honjo M., Furukawa Y., Nishikawa M., Kamiya K., Yoshida Y., Chem. Pharm. Bull., 15, 1076-1079 (1967).
15. a) Ueda T., Usui H., Shuto S., Inoue H., Chem. Pharm. Bull., 32, 3410-3416 (1984);
16. b) Yoshimura Y., Otter B. A., Ueda T., Matsuda A., ibid., 40, 1761-1769 (1992).
17. a) Ikehara M., Kaneko M., Chem. Pharm. Bull., 15, 1261-1262 (1967);
18. b) Ikehara M., Maruyama T., Tetrahedron, 31, 1369-1372 (1975).
19. Biggadike K., Borthwick A. D., Evans D., Exall A. M., Kirk B. E., Roberts S. M., Stephenson L., Youds P., J. Chem. Soc., Perkin Trans. 1, 1988, 549-554.
20. Partridge J. J., Chadha N. K., Uskokovic M. R., J. Am. Chem. Soc., 95, 532-540 (1973).
21. The numbering system used for carbocyclic nucleosides in reference 17 is employed in the text and Experimental section to facilitate comparison of the NMR spectra. In this nomenclature, the carbon atom replacing the furanose ring oxygen of natural nucleosides is designated C-6′.
22. a) Biggadike K., Borthwick D., Exall A. M., Kirk B. E., Roberts S. M., Youds P., J. Chem. Soc., Chem. Commun., 1987, 1083-1084;
23. b) Borthwick A. D., Biggadike K., Tetrahedron, 48, 571-623 (1992).
24. Kumar R., Wiebe L. I., Knaus E. E., Can. J. Chem., 72, 2005-2010 (1994).
25. Sano T., Shuto S., Inoue H., Ueda T., Chem. Pharm. Bull., 33, 3617-3622 (1985).
26. Divakar K. J., Reese C. B., J. Chem. Soc., Perkin Trans, 1, 1982, 1171 -1176.
27. Maruyama T., Sato S., Honjo M., Chem. Pharm. Bull., 30, 2688-2697 (1982).
28. Kawahata T., Otake T., Mori H., Morimoto M., Ueba N., Kusumoto I. T., El-Mekkawy S., Hattori M., Namba T., J. Traditional Med., 13, 59-65 (1996).