Synthesis and metabolism of naphthyl substituted phosphoramidate derivatives of stavudine

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 15, 2006, Pages 5161-5177

  Venkatachalam, T K ^a,b   Qazi, S ^a,b   Uckun, F M ^a,b  

^a PARKER HUGHES INSTITUTE   (United States)

^b Paradigm Pharmaceuticals   (United States)

Author keywords

Metabolism; Naphthyl; Phosphoramidate; Synthesis

Indexed keywords

CARICA PAPAYA EXTRACT; ESTERASE; NAPHTHALENE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; PROTEINASE; STAVUDINE; STAVUDINE 5' ALPHA NAPHTHYLMETHOXYALANINE PHOSPHATE; STAVUDINE 5' BETA NAPHTHYLMETHOXYALANINE PHOSPHATE; SUBTILISIN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DERIVATIZATION; DRUG SYNTHESIS; HYDROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

AMIDES; CARICA; ESTERASES; HYDROLYSIS; LIPASE; MOLECULAR STRUCTURE; NAPHTHALENES; PHOSPHORIC ACIDS; SERINE ENDOPEPTIDASES; STAVUDINE; STEREOISOMERISM; SUBTILISINS; TIME FACTORS;

CARICA PAPAYA;

EID: 33745139879     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.04.006     Document Type: Article

References (41)

1. Goldschmidt R.H., and Dong B.J. J. Am. Board of Fam. Pract. 10 (1997) 144-167
2. Deeks S.G., and Volberding P.A. AIDS Clin. Rev (1997-1998) 145
3. Grob P.M., Wu J.C., Cohen K.A., Ingraham R.H., Shih C.K., Hargrave K.D., Mctague T.L., and Merluzzi V.J. AIDS Res. Hum. Retrovirus 8 (1992) 145
4. Bell F.W., Cantrell A.S., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kinnick M.D., Lind P., Morin Jr. J.M., Noreen R., Oberg B., Palkowitz J.A., Parrish C.A., Pranc P., Sahlberg C., Ternansky R.T., Vasileff R.T., Vrang L., West S.J., Zhang H., and Zhou X.X. J. Med. Chem. 38 (1995) 4929
5. Cantrell A.S., Engelhardt P., Hogberg M., Jaskunas S.R., Johansson N.G., Jordan C.L., Kangasmetsa J., Kinnick M.D., Lind P., Morin Jr. J.M., Muesing M.A., Noreen R., Oberg B., Pranc P., Sahlberg C., Ternansky R.J., Vasileff R.T., Vrang L., West S.J., and Zhang H. J. Med. Chem. 39 (1996) 4261
6. Vig R., Venkatachalam T.K., and Uckun F.M. Antiviral Chem. Chemother. 9 (1998) 445
7. Mao C., Vig R., Venkatachalam T.K., Sudbeck E.A., and Uckun F.M. Bioorg. Med. Chem. Lett. 8 (1998) 2213
8. Furman P.A., Fyfe J.A., Clair M.H.St., Weinhold K., Rideout J.L., Freeman G.A., Nusinoff L.S., Bolognesi D.P., Broder S., Mitsuya H., and Barry D.W. Proc. Natl. Acad. Sci. U.S.A. 83 (1986) 8333
9. Hao Z., Cooney D.A., Hartman N.R., Perno C.F., Fridland A., De Vico A.L., Sarngadharan M.G., Border S., and Johns D.G. Mol. Pharmacol. 34 (1988) 431
10. Balzarini J., Cooney D.A., Dalal M., Kang G.J., Cupp J.E., De Clercq E., Broder S., and Johns D.G. Mol. Pharmacol. 32 (1987) 798
11. McGuigan C., Cahard D., Sheeka H.M., De Clercq E., and Balzarini J. J. Med. Chem. 39 (1996) 1748
12. McGuigan C., Cahard D., Sheeka H.M., De Clercq E., and Balzarini J. Bioorg. Med. Chem. Lett. 6 (1996) 1183
13. Starnes M.G., and Cheng Y.C. J. Biol. Chem. 262 (1987) 988
14. Hao Z., Cooney D.A., Farquhar D., Perno C.F., Zhang K., Masood R., Wilson Y., Hartman N.R., Balzarini J., and Johns D.G. Mol. Pharmacol. 37 (1990) 157
15. Johnson M.A., Ahluwalia G., Connelly M.C., Cooney D.A., Broder S., Johns D.G., and Fridland A. J. Biol. Chem. 263 (1988) 15354
16. Johnson M.A., and Fridland A. Mol. Pharmacol. 36 (1989) 291
17. McGuigan C., Pathirana R.N., Balzarini J., and De Clercq E. J. Med. Chem. 36 (1993) 1048
18. McGuigan C., Pathirana R.N., Mahmood N., Devine K.G., and Hay A. J. Antiviral Res. 17 (1992) 311
19. Vig R., Mao C., Venkatachalam T.K., Tuel-Ahlgren L., Sudbeck E.A., and Uckun F.M. Bioorg. Med. Chem. (1998) 1789
20. Venkatachalam T.K., Tai T.L., Vig R., Chen C.L., Jan S.T., and Uckun F.M. Bioorg. Med. Chem. Lett. 8 (1998) 3121
21. Uckun F.M., Samuel P., Qazi S., Chen C.L., Pendergrass S., and Venkatachalam T.K. Antiviral Chem. Chemother. 13 (2002) 197
22. Siccardi D., Gumbleton M., Omidi Y., and McGuican C. Eur. J. Pharm. Sci. 22 (2004) 25
23. Congiatu C., McGuican C., Jiang W.G., Davies G., and Mason M.D. Nucleosides Nucleotides Nucleic acids 24 (2005) 485
24. Congiatu C., Brancale A., Mason M.D., Jiang W.G., and McGuican C. J. Med.Chem. 49 (2006) 452
25. Venkatachalam T.K., Samuel P., Li G., Qazi S., Mao C., Pendergrass S., and Uckun F.M. Bioorg. Med.Chem. 12 (2004) 3371
26. Venkatachalam T.K., Samuel P., Qazi S., and Uckun F.M. Eur. J. Med. Chem. 40 (2005) 452
27. Chapman H., Kernan E., Prisbe E., Rohloff J., Sparacino M., Terhorst T., and Yu R. Nucelosides Nucleic Acids 20 (2001) 621
28. Chapman H., Kernan E., Rohloff J., Sparacino M., and Terhorst T. Nucelosides Nucleic Acids 20 (2001) 1085
29. Meier C., Lorey M., De Clercq E., and Balzarini J. J. Med. Chem. 41 (1998) 417
30. Meier C., Knispel T., De Clercq E., and Balzarini J. J. Med. Chem. 42 (1999) 1604
31. McGuigan C., Devine K.G., O'Conor T.J., Galpin S.A., Jeffries D.J., and Kinchington D. Antiviral Chem. Chemother 1 (1990) 107
32. Venkatachalam T.K., Qazi S., and Uckun F.M. Drug Res. 56 (2006) 152
33. Venkatachalam, T. K.; Marquis, S.; Qazi, S.; Uckun, F. M. Under preparation.
34. McIntee E.J., Remmel R.P., Schinazi R.F., Abraham T.W., and Wagner C.R. J. Med. Chem. 40 (1997) 3323
35. Balzarini J., Karlsson A., Aquaro S., Perno C.F., Cahard D., Naesens L., et al. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 7295
36. Balzarini J., Egberink H., Hartman D., Cahard D., Vahlenkamp T., Thormar H., et al. Mol. Pharmacol. 50 (1996) 1207
37. Abraham T.W., and Wagner C.R. Nucleosides Nucleotides 13 (1994) 1891
38. Devedjiev I., Petrova K., and Glavchev I. Syn. Commun. 30 (2000) 4411
39. Devedjiev I., and Borisov G. Phosphorous, Sulfur Silicon Relat. Elem. 53 (1990) 37
40. Tzokov S.B., Devedjiev I., and Petkov D. J. Org. Chem. 61 (1996) 12
41. Tzokov S.B., Devedjiev I., Bratovanova E., and Petkov D. Angew. Chem. Int. Ed. Engl. 33 (1994) 2302