Synthesis of dinucleotide thiophosphoramidates as anti-HIV new prodrugs

Synthesis

Volumn , Issue 13, 2003, Pages 1989-1994

  Lin, Changxue ^a   Fu, Hua ^a   Tu, Guangzhong ^b   Zhao, Yufen ^a  

^a TSINGHUA UNIVERSITY   (China)

^b BEIJING INSTITUTE OF MICROCHEMISTRY   (China)

Author keywords

Antiviral agents; Drugs; Esterification; Nucleotides; Phosphorus

Indexed keywords

CONDENSATION; DRUG PRODUCTS; ESTERS; ORGANIC ACIDS;

METHYL ESTERS;

SYNTHESIS (CHEMICAL);

1 [2,5 DIHYDRO 5 [(3' O THYMIDINYL)(METHOXYALANYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [2,5 DIHYDRO 5 [(3' O THYMIDINYL)(METHOXYGLYCYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [2,5 DIHYDRO 5 [(3' O THYMIDINYL)(METHOXYISOLEUCYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [2,5 DIHYDRO 5 [(3' O THYMIDINYL)(METHOXYLEUCYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [2,5 DIHYDRO 5 [(3' O THYMIDINYL)(METHOXYPHENYLALANYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [2,5 DIHYDRO 5 [(3' O THYMIDINYL)(METHOXYVALYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [4 AZIDOTETRAHYDRO 5 [(3' O THYMIDINYL)(METHOXYALANYL)]METHYL 2 FURYL]THYMINE; 1 [4 AZIDOTETRAHYDRO 5 [(3' O THYMIDINYL)(METHOXYGLYCYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [4 AZIDOTETRAHYDRO 5 [(3' O THYMIDINYL)(METHOXYISOLEUCYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [4 AZIDOTETRAHYDRO 5 [(3' O THYMIDINYL)(METHOXYLEUCYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 1 [4 AZIDOTETRAHYDRO 5 [(3' O THYMIDINYL)(METHOXYPHENYLALANYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE; 5' O DIMETHOXYTRITYLTHYMIDINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; FORMIC ACID; NUCLEOTIDE DERIVATIVE; O (5' DIMETHOXYTRITYL 2' DEOXYTHYMIDIN 3' YL) O (2',3' DIDEOXYTHYMIDIN 5' YL) H THIOPHOSPHONATE; O (5' DIMETHOXYTRITYL 2' DEOXYTHYMIDIN 3' YL) O (3' AZIDO 2' DEOXYTHYMIDIN 5' YL) H THIOPHOSPHONATE; O [5' O (4,4' DIMETHOXYTRITYL)THYMIDIN 3' YL] H THIOPHOSPHONATE; PRODRUG; UNCLASSIFIED DRUG; [4 AZIDOTETRAHYDRO 5 [(3' O THYMIDINYL)(METHOXYVALYL)PHOSPHORYL]METHYL 2 FURYL]THYMINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; ESTERIFICATION; MASS SPECTROMETRY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141841594     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41039     Document Type: Article

References (28)

1. Ueno, T.; Mitsuya, H. Clin. Immunother. 1995, 4, 451.
2. Boussard, C.; Doyle, V. E.; Mahmood, N.; Klimkait, T.; Pritchard, M.; Gilbert, I. H. Eur. J. Med. Chem. 2002, 37, 883.
3. (a) Vlieghe, P.; Clerc, T.; Pannecouque, C.; Witvrouw, M.; De Clercq, E. ; Salles, J. P.; Kraus, J. L. J. Med. Chem. 2002, 45, 1275.
4. (b) Wong, A.; Toth, I. Curr. Med. Chem. 2001, 8, 1123.
5. (c) Gallo, J. M. Adv. Drug Deliver Rev. 1994, 14, 199.
6. (a) Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; Clair, M. H. Proc. Natl. Acad. Sci. U. S. A. 1985, 82, 7096.
7. (b) Rando, R. F.; Nguyen-Ba, N. Drug Discovery Today 2000, 5, 465.
8. (c) Fischl, M. A.; Richman, D. D.; Grieco, M. H.; Gottlieb, M. S. N. Engl. J. Med. 1987, 317, 185.
9. Wanger, C. R.; Iyer, V. V.; McIntee, E. J. Med. Res. Rev. 2000, 20, 417.
10. (a) Richman, D. D.; Fischl, M. A.; Grieco, M. H.; Gottlieb, M. S.; Volberding, P. A.; Laskin, O. L.; Leedon, J. M.; Groopman, J. E.; Mildvan, D.; Hirsch, M. S.; Jackson, G. G.; Durack, D. T.; Nusinoff-Lehrman, S. N. Engl. J. Med. 1987, 317, 192.
11. (b) Pan-Zhou, X. R.; Cretton-Scott, E.; Zhou, X. J.; Yang, M. X.; Lasker, J. M.; Sommadossi, J. P. Biochem. Pharmacol. 1998, 55, 757.
12. (c) Trapnell, C. B.; Klecker, R. W.; Jamisdow, C.; Collins, J. M. Antimicrob. Agents. Chemother. 1998, 42, 1592.
13. (a) Larder, B. A.; Darby, G.; Richman, D. D. Science 1989, 243, 1731.
14. (b) Kallam, P.; Boucher, C. A. B.; Larde, B. A. Proc. Natl. Acad. Sci. U. S. A. 1992, 89, 1934.
15. (c) Rando, R. F.; Nguyen-Ba, N. Drug Discovery Today 2000, 5, 465.
16. (a) Parang, K.; Wiebe, L. I.; Knaus, E. E. Curr. Med. Chem. 2000, 7, 995.
17. (b) Sergheraert, C.; Pierlot, C.; Tartar, A.; Henin, Y.; Lemaitre, M. J. Med. Chem. 1993, 36, 826.
18. (c) Hostetler, K. Y.; Stuhmiller, L. M.; Lenting, H. B. M.; van den Bosch, H.; Richman, D. D. J. Biol. Chem. 1990, 265, 6112.
19. Busso, M.; Mian, A. M.; Hahn, E. F.; Resnick, L. AIDS Res. Hum. Retroviruses 1988, 4, 449.
20. Shinazi, R. F.; Sommadossi, J. P.; Saalmann, V.; Cannon, D. L.; Xie, M. Y.; Hart, G. C.; Smith, G. A.; Hahn, E. F. Antimicrob. Agents Chemother. 1990, 34, 1061.
21. De Clerq, E. Nucleosides Nucleotides Nucleic Acids 1994, 13, 1271.
22. Stein, C. A. Nucleic Acids Res. 1988, 16, 3209.
23. (a) McGuigan, C.; Devine, K. G.; O'Connor, T. J.; Galpin, S. A.; Jeffries, J. D.; Kinchington, D. Antiviral Chem. Chemother. 1990, 1, 107.
24. (b) McGuigan, C.; Devine, K. G.; O'Connor, T. J.; Kinchington, D. Antiviral Res. 1991, 15, 255.
25. (a) Atherton, F. R.; Openshaw, H. T.; Todd, A. R. J. Chem. Soc. 1945, 660.
26. (b) Atherton, F. R.; Todd, A. R. J. Chem. Soc. 1947, 674.
27. Peyser, J. R.; Ferris, J. P. Orig. Life Evol. Biosph. 2001, 31, 363.
28. Kers, I.; Kers, A.; Stawinski, J. Tetrahedron Lett. 1999, 40, 3945.