Synthesis of phosphonate isosteres of 2′-deoxy-1′,2′-seco-nucleotides

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 890-894

  El Subbagh, Hussein I ^a   Racha, Saibaba ^a   Abushanab, Elie ^a   Panzica, Raymond P ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANINE DERIVATIVE; NUCLEOTIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; THYMINE DERIVATIVE; URACIL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030024975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951701v     Document Type: Article

References (23)

1. (a) Engel, R. Chem. Rev. 1977, 77, 349 and references cited therein.
2. (b) Krayevsky, A. A.; Watanabe, K. A. Modified Nucleosides as Anti-Aids Drugs: Current Status and Perspectives; Bioinform: Moscow, 1993; pp 98-125.
3. Mikhailov, S. N.; Podyukova, N. Sh.; Karpeiskii, M. Ya.; Kolobushkina, L. I.; Beigelman, L. N. Collect. Czech, Chem. Commun. 1989, 54, 1055.
4. Aimer, H.; Classon, B.; Samuelsson, B.; Kvarnstrom, I. Acta Chem. Scand. 1991, 45, 766.
5. (a) Ioannidis, P.; Classon, B.; Samuelsson, B.; Kvarnstrom, I. Acta Chem. Scand. 1991, 45, 746.
6. (b) Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563.
7. (a) Wolff-Kugel, D.; Halazy, S. Nucleosides Nucleotides 1993, 12, 279.
8. (b) Charron, M; Tse, H. L. A.; Mansour, T. S.; Knight, D. J.; O'Sullivan, C.; Coates, J. A. V. Heteroatom Chem. 1994, 5, 491.
9. Li, Z., Racha, S., Dan, L.; El-Subbagh, H. I.; Abushanab, E. J. Org Chem. 1993, 58, 5779.
10. In the text, the naming and numbering of the 1′,2′-seco-nucleophosphonates follow nucleoside nomenclature.
11. Reist, E. J.; Sturm, P. A.; Pong, R. Y.; Tanga, M. J. Sidwell. R. W. Synthesis of Acyclonucleoside Phosphonates for Evaluation as Antiviral Agents. In Nucleotide Analogues as Antiviral Agents; Martin, J. C., Ed.; American Chemical Society: Washington, DC, 1989; pp 17-34.
12. (a) Prisbe, E. J.; Martin, J. C.; McGee, D. P. C.; Barker, M. F. Smee, D. F.; Duke, A. E. Matthews, T. R.; Verheyden, J P. H. J. Med. Chem. 1985, 29, 671.
13. (b) Chamberlain, S. D.; Biron, K. K.; Dornsife, R. E.; Averett, D. R.; Beauchamp, L.; Koszalka, G. W. J. Med. Chem. 1994, 37, 1371.
14. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkileneni, A. B.; Wu, D. C.-J ; Racha, S.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598.
15. (a) Vemishetti, P.; Leiby, R. W.; Abushanab, E.; Panzica, R. P. J. Heterocycl. Chem. 1988, 25, 651.
16. (b) Vemishetti, P.; Saibaba, R.; Panzica, R. P ; Abushanab, E. J. Med. Chem. 1990, 33, 681.
17. 5P) C, H, N.
18. Mazur, A.; Tropp, B. E.: Engel, R. Tetrahedron 1984, 40, 3949.
19. Unpublished data.
20. Garbay-Jaureguiberry, C.; Ficheux, D.; Roques, B. P. Int. J. Pept. Protein Res. 1992, 39, 523.
21. (a) Kruerke, U. Chem Ber. 1962, 95, 174.
22. (b) Kumada, M.; Hattori, H. Chem Abstr. 1954, 48, 7542a.
23. Cichy, A. E. The Synthesis of 4′-Iso-1′,2′-Seco-Nucleosides and Nucleotides as Potential Enzyme Inhibitors, Ph.D. Thesis, University of Rhode Island, Kingston, RI, 1989.