Synthesis, bioactivation and anti-hiv activity of 4-acyloxybenzyl bis(nucleosid-5‘-yl) phosphates

Nucleosides and Nucleotides

Volumn 14, Issue 7, 1995, Pages 1545-1558

  Freeman, Sally ^a,e   Walker, Ian ^a   Hay, Alan ^b   Mahmood, Naheed ^c  

^a ASTON UNIVERSITY   (United Kingdom)

^b NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

^c MEDICAL RESEARCH COUNCIL   (United Kingdom)

^d UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^e UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 ACYLOXYBENZYL BIS(NUCLEOSID 5' YL) PHOSPHATE; CARBOXYLESTERASE; PRODRUG; THYMIDINE KINASE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; BIODEGRADATION; BONE MARROW SUPPRESSION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME DEFICIENCY; HUMAN IMMUNODEFICIENCY VIRUS; VIRUS RESISTANCE;

EID: 0029155592     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257779508009491     Document Type: Article

References (38)

1. Mitsuya, H.; Weinhold, K.J.; Furman, P.A.; St Clair, M.H.; Nusinoff-Lehrman, S.; Gallo, R.C.; Bolognesi, D.; Barry, D.W.; Broder, S., Proc. Natl. Acad. Sci., U.S.A. 1985, 82, 7096.
2. Yarchoan, R.; Mitsuya, H.; Broder, S., Scientific American, 1988, 259, No.4, 88.
3. Yarchoan, R.; Weinhold, K.J.; Lyerly, H.K.; Gelmann, E.; Blum, R.M.; Shearer, G.M.; Mitsuya, H.; Collins, J.M.; Myers, C.E.; Klecker, R.W.; Markham, P.D.; Durack, D.T.; Nusinoff-Lehrman, S.; Barry, D.W.; Fischl, M.A.; Gallo, R.C.; Bolognesi, D.P.; Broder, S., Lancet, 1986, 1, 575.
4. Larder, B.A.; Kemp, S.D., Science, 1989, 246, 1155.
5. Richman, D.D.; Fischl, M.A.; Grieco, M.H.; Gottlieb, M.S.; Volberding, P.A.; Laskin, O.L.; Leedom, J.M.; Groopman, J.E.; Mildvan, D.; Hirsch, M.S.; Jackson, G.G.; Durack, D.T.; Nusinoff-Lehrman, S., N. Eng. J. Med., 1987, 317, 192.
6. Mitsuya, H.; Broder, S., Proc. Natl. Acad. Sci. U.S.A., 1986, 83, 1911.
7. Hamamoto, Y.; Nakashima, H.; Matsui, T.; Matsuda, A.; Ueda, T.; Yamamoto, N., Antimicrob. Agents Chemother., 1987, 31, 907.
8. Cooney, D.A.; Dalai, M.; Mitsuya, H.; McMahon, J.B.; Nadkami, M.; Balzarini, J.; Broder, S.; Johns, D.G., Biochem. Pharmacol., 1986, 35, 2065.
9. Heidenreich, O.; Eckstein, F., Nucleosides Nucleotides, 1991, 10, 535.
10. Bungaard, H., in Design of Prodrugs, ed. Bungaard, H., Elsevier, Amsterdam, 1985, pp. 70-74.
11. Thomson, W.; Nicholls, D.; Irwin, W.J.; Al-Mushadani, J.S.; Freeman, S.; Karpas, A.; Petrik, J.; Mahmood, N.; Hay, A.J., J. Chem. Soc. Perkin Trans. I, 1993, 1239.
12. Henin, Y.; Gouyette, C.; Schwartz, O.; Debouzy, J.-C.; Neumann, J.-M.; Huynh-Dinh, T., J. Med. Chem., 1991, 34, 1830.
13. Le Bee, C.; Huynh-Dinh, T., Tetrahedron Lett., 1991, 32, 6553.
14. McGuigan, C.; Nicholls, S.R.; O’Connor, T.J.; Kinchington, D., Antiviral Chem. Chemother., 1990, 1, 25.
15. Jones, B.C.N.M.; McGuigan, C.; O’Connor, T.J.; Jeffries, D.J.; Kinchington, D., Antiviral Chem. Chemother., 1991, 2, 35.
16. Meier, C., Angew. Chem. Int. Ed. Engl., 1993, 32, 1704.
17. Perigaud, C.; Gosselin, G.; Lefebvre, I.; Girardet, J.-L.;Benzaria, S.; Barber, I.; Imbach, J.-L., Bioorg. Med. Chem. Lett., 1993, 3, 2521.
18. Perigaud, C.; Aubertin, A.-M.; Benzaria, S.; Pelicano, H.; Girardet, J.-L.; Maury, G.; Gosselin, G.; Kim, A.; Imbach, J.-L., Biochem. Pharmacol., 1994, 48, 11.
19. Farquhar, D.; Khan, S.; Srivastva, D.N.; Saunders, P.P., J. Med. Chem., 1994, 37, 3902.
20. Starrett Jr, J.E.; Tortolani, D.R.; Russell, J.; Hitchcock, J.M.; Whiterock, V.; Martin, J.C.; Mansuri, M.M., J. Med. Chem., 1994, 37, 1857.
21. Farquhar, D.; Chen, R.; Khan, S., J. Med. Chem., 1995, 38, 488.
22. Shimizu, S.I.; Balzarini, J.; De Clercq, E.; Walker, R.T., Nucleosides Nucleotides, 1992, 11, 583.
23. Hahn, E.F.; Busso, M.; Mian, A.M.; Resnick, L., Nucleotide Analogues as Antiviral Agents, ACS Symposium Series 401, ACS, Washington D.C., 1989, pp. 156-169.
24. Meier, C.; Neumann, J.-M.; Andre, F.; Henin, Y.; Huynh-Dinh, T., J. Org. Chem., 1992, 57, 7300.
25. Grice, R.; Owen, L.N., J. Chem. Soc., 1963, 1947.
26. Perich, J.W.; Johns, R.B., Synthesis, 1988, 142.
27. Boudjebel, H.; Concalves, H.; Mathis, F., Bull. Soc. Chim. Fr., 1975, 628.
28. Bannwarth, W.; Trzeciak, A., Helv. Chimica. Acta, 1987, 70, 175.
29. Busso, M.; Mian, A.M.; Hahn, E.F.; Resnick, L., AIDS Res. Hum. Retrov., 1988, 4, 449.
30. Zervas, L.; Dilaris, I., J. Am. Chem. Soc., 1955, 77, 5354.
31. Fife, T.H.; Bruice, T.C., J. Phys. Chem., 1961, 65, 1079.
32. Balzarini, J.; Herdewijn, P.; Pauwels, R.; Broder, S.; De Clercq, E., Biochem. Pharmacol., 1988, 37, 2395.
33. Puech, F.; Gosselin, G.; Balzarini, J.; De Clercq, E.; Imbach, J.-L., J. Med. Chem., 1988, 31, 1897.
34. Puech, F.; Pompon, A.; Lefebvre, I.; Gosselin, G.; Imbach, J.-L., Bioorg. Med. Chem. Lett., 1992, 2, 603.
35. Pompon, A.; Lefebvre, I.; Imbach, J.-L.; Kahn, S.; Farquhar, D., Antiviral Chem. Chemother., 1994, 5, 91.
36. Still, W.C.; Kahn, M.; Mitra, A., J. Org. Chem., 1978, 43, 2923.
37. Mahmood, N.; Hay, A.J., J. Immunol. Methods, 1992, 151, 9.
38. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E., J. Virol. Methods, 1988, 20, 309.