Synthesis and antiviral activity of boranophosphonate isosteres of AZT and d4T monophosphates

European Journal of Medicinal Chemistry

Volumn 45, Issue 2, 2010, Pages 849-856

  Barral, Karine ^a   Priet, Stéphane ^a   De Michelis, Céline ^a   Sire, Joséphine ^b   Neyts, Johan ^c   Balzarini, Jan ^c   Canard, Bruno ^a   Alvarez, Karine ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b Aix Marseille University IRD 190 Inserm 1207   (France)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral activity; AZT and d4T analogues; Boranophosphonate; Metabolism; Modified nucleotide

Indexed keywords

1 (2' DEOXY 3', 5' EPOXY BETA DEXTRO THREO PENTOFURANOSYL)THYMINE; 1 [2',3' DIDEHYDRO 2',3',5',6' TETRADEOXY 6' (BORANOPHOSPHONO)BETA HEXOFURANOSYL]THYMINE; 1 [2',3' DIDEHYDRO 2',3',5',6' TETRADEOXY 6' (DIETHOXYPHOSPHONYL)BETA HEXOFURANOSYL]THYMINE; 1 [2',3' DIDEHYDRO 2',3',5',6' TETRADEOXY 6' (HYDROXYPHOSPHINYL)BETA HEXOFURANOSYL]THYMINE; 1 [2',3' DIDEHYDRO 2',3',5',6' TETRADEOXY 6' (PHOSPHANYL)BETA HEXOFURANOSYL]THYMINE; 1 [2',5',6' TRIDEOXY 6' (DIETHOXYPHOSPHONYL)BETA HEXOFURANOSYL]; 1 [3' AZIDO 2',3',5',6' TETRADEOXY 6' (BORANOPHOSPHONO)BETA HEXOFURANOSYL]THYMINE; 1 [3' AZIDO 2',3',5',6' TETRADEOXY 6' (HYDROXYPHOSPHINYL)BETA HEXOFURANOSYL]THYMINE; 1 [3' O MESYL 2',5',6' TRIDEOXY 6 (DIETHOXYPHOSPHONYL)BETA HEXOFURANOSYL]THYMINE; 1 [3' O MESYL 2',5',6' TRIDEOXY 6' (HYDROXYPHOSPHINYL)BETA HEXOFURANOSYL]THYMINE; 1 [3' O MESYL 2',5',6' TRIDEOXY 6' (PHOSPHANYL)BETA HEXOFURANOSYL]THYMINE; 2',3' DIDEHYDRO 3' DIDEOXYTHYMIDINE 5' BORANOPHOSPHONATE; 3' AZIDO 3' DEOXYTHYMIDINE 5' BORANOPHOSPHONATE; ACICLOVIR; ANTIVIRUS AGENT; CIDOFOVIR; GANCICLOVIR; STAVUDINE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CULTURE MEDIUM; DRUG ACTIVITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; IN VITRO STUDY;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; DRUG STABILITY; HALF-LIFE; HUMANS; PHOSPHONIC ACIDS; STAVUDINE; VIRUSES; ZIDOVUDINE;

EID: 73849111027     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.11.012     Document Type: Article

References (39)

1. Furman P.A., Fyfe J.A., St Clair M.H., Weinhold K., Rideout J.L., Freeman G.A., Nusinoff Lehrman S., Bolognesi D.P., Broder S., Mitsuya H., and Barry D.W. Proceedings of the National Academy of Sciences of the United States of America 83 (1986) 8333-8337
2. Baba M., Pauwels R., Herdewijn P., De Clercq E., Desmyter J., and Vandeputte M. Biochemical and Biophysical Research Communications 142 (1987) 128-134
3. Yarchoan R., Mitsuya H., Meyer C.E., and Broder S. New England Journal of Medecine 321 (1989) 726-738
4. Reardon J.E., and Miller W.H. Journal of Biological Chemistry 265 (1990) 20302-20307
5. Declercq E. Journal of Antimicrobial Chemotherapy 23 (1989) 35-46
6. Arion D., Kaushik N., Mc Cormick S., Borkow G., and Parniak M.A. Biochemistry 37 (1998) 15908-15917
7. Selmi B., Boretto J., Sarfati S.R., Guerreiro C., and Canard B. The Journal of Biological Chemistry 276 (2001) 48466-48472
8. Alvarez K., Deval J., Selmi B., Barral K., Boretto J., Guerreiro C., Mulard L., Sarfati S., and Canard B. Nucleosides, Nucleotides & Nucleic Acids 24 (2005) 419-422
9. Schneider B., Meyer P., Sarfati S., Mulard L., Guerreiro C., Boretto J., Janin J., Veron M., Deville-Bonne D., and Canard B. Nucleosides, Nucleotides & Nucleic Acids 20 (2001) 297-306
10. Meyer P., Schneider B., Sarfati S., Deville-Bonne D., Guerreiro C., Boretto J., Janin J., Veron M., and Canard B. EMBO Journal 19 (2000) 3520-3529
11. Deval J., Alvarez K., Selmi B., Bermond M., Boretto J., Guerreiro C., Mulard L., and Canard B. Journal of Biological Chemistry 280 (2005) 3838-3846
12. Pompon A., Lefebvre I., Imbach J.-L., Kahn S., and Farquhar D. Antiviral Chemistry & Chemotherapy 5 (1994) 91-98
13. Meier C., Lorey M., De Clercq E., and Balzarini J. Journal of Medicinal Chemistry 41 (1998) 1417-1427
14. Engel R. Chemical Reviews 77 (1977) 349-367
15. Frangeul A., Barral K., Alvarez K., and Canard B. Antimicrobial Agents and Chemotherapy 51 (2007) 3162-3167
16. Sergueeva Z.A., Sergueev D.S., and Shaw B.R. Nucleosides Nucleotides Nucleic Acids 20 (2001) 941-945
17. Sergueev D.S., and Ramsay Shaw B. Journal of the American Chemical Society 120 (1998) 9417-9427
18. Barral K., Priet S., Sire J., Neyts J., Balzarini J., Canard B., and Alvarez K. Journal of Medicinal Chemistry 49 (2006) 7799-7806
19. Lavandera I., Fernandez S., Ferreo M., and Gotor V. Journal of Organic Chemistry 66 (2001) 4079-4082
20. Horwitz J.P., Chua J., Urbanski J.A., and Noel M. Journal of Organic Chemistry 28 (1963) 942-944
21. Paramashivappa R., Kumar P., Subba Rao P.V., and Srinivasa Rao A. Tetrahedron Letters 44 (2003) 1003-1005
22. Tanaka H., Fukui M., Haraguchi K., Masaki M., and Miyasaka T. Tetrahedron Letters 30 (1989) 2567-2570
23. Haraguchi K., Tanaka H., and Miyasaka T. Synthesis 6 (1989) 434-436
24. Hutter D., Blaettler M.O., and Benner S.A. Helvetica Chimica Acta 85 (2002) 2777-2806
25. Kyba E.P., Liu S.-T., and Harris R.L. Organometallics 2 (1983) 1877-1879
26. Henderson W., and Alley S.R. Journal of Organometallic Chemistry 656 (2002) 120-128
27. Reiter S.A., Assmann B., Nogai S.D., Mitzel N.W., and Schmidbaur H. Helvetica Chimica Acta 85 (2002) 1140-1150
28. Yamamoto H., Hanaya T., Kawamoto H., Inokawa S., Yamashita M., Armour M.-A., and Nakashima T.T. Journal of Organic Chemistry 50 (1985) 3516-3521
29. Molin H., Noren J.-O., and Claesson A. Carbohydrate Research 194 (1989) 209-221
30. Kvaerno L., Wightman R.H., and Wengel J. Journal of Organic Chemistry 66 (2001) 5106-5112
31. Dhotare B., and Chattopadhyay A. Synthesis-Stuttgart (2001) 1337-1340
32. Wada T., Mochizuki A., Sato Y., and Sekine M. Tetrahedron Letters 39 (1998) 7123-7126
33. He K., Porter K.W., Hasan A., Briley J.D., and Shaw B.R. Nucleic Acids Research 27 (1999) 1788-1794
34. Li P., and Shaw B.R. Organic Letters 4 (2002) 2009-2012
35. Li H., Hardin C., and Shaw B.R. Journal of the American Chemical Society 118 (1996) 6606-6614
36. Chen J.J., Wei Y., Drach J.C., and Townsend L.B. Journal of Medicinal Chemistry 43 (2000) 2449-2456
37. Puech F., Gosselin G., Lefebvre I., Pompon A., Aubertin A.M., Kirn A., and Imbach J.L. Antiviral Research 22 (1993) 155-174
38. Kim C.U., Bronson J.J., Ferrara L.M., and Martin J.C. Bioorganic & Medicinal Chemistry Letters 2 (1992) 367-370
39. O'Doherty U., Swiggard W.J., and Malim M.H. Journal of Virology 74 (2000) 10074-10080