Synthesis and anti-HIV1 biological activity of novel 5″-ATSAO compounds

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 8, 2008, Pages 4733-4741

  Tomassi, Cyrille ^a   Nguyen Van Nhien, Albert ^a   Marco Contelles, José ^b   Balzarini, Jan ^c   Pannecouque, Christophe ^c   De Clercq, Erik ^c   Postel, Denis ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

ATSAO; CSIC reaction; Glycoaminonitrile; NNRTI; TSAO

Indexed keywords

2',5' BIS O (TER BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3' SPIRO 5'' (4' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE)THYMINE; [1 [2',5' BIS O TERT BUTYLDIMETHYSILYL BETA DEXTRO RIBOFURANOSYL] 3 N ETHYLTHYMINE 3' SPIRO 3'' (2'' H 4'' AMINO 2'',3'' DIHYCRO 1'',1'' DIOXO ISOTHIAZOLE 5'' PHENYL); [1 [2',5' BIS O TERT BUTYLDIMETHYSILYL BETA DEXTRO RIBOFURANOSYL] 3 N METHYLTHYMINE 3' SPIRO 3'' (2'' H 4'' AMINO 2'',3'' DIHYCRO 1'',1'' DIOXO ISOTHIAZOLE 5'' PHENYL); [1 [2',5' BIS O TERT BUTYLDIMETHYSILYL BETA DEXTRO RIBOFURANOSYL] 3 N METHYLTHYMINE 3' SPIRO 3'' (4'' H 2'',3'' DIHYDRO 2'' N METHYL 1'',1'' DIOXO ISOTHIAZOLE 5'' PHENYL); HUMAN IMMUNODEFICIENCY VIRUS ANTIBODY; THYMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

ANTI-HIV AGENTS; AZA COMPOUNDS; HIV-1; MOLECULAR STRUCTURE; NUCLEOSIDES; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 42149114258     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.026     Document Type: Article

References (26)

1. Restle T., Muller B., and Godoy R.S. J. Biol. Chem. 265 (1990) 8986-8988
2. Wang J., Smerdon S.J., Jager J., Kohlstaedt L.A., Rice P.A., Friedman J.M., and Steitz T.A. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 7242-7246
3. Pandey P.K., Kaushik N., Talele T.T., Yadav P.N.S., and Pandey V.N. Biochemistry 40 (2001) 9505-9512
4. Pandey P.K., Kaushik N., Singh K., Sharma B., Upadhyay A.K., Kumar S., Harris D., and Pandey V.N. BMC Biochem. 3 (2002) 18-31
5. Camarasa M.-J., Pérez-Pérez M.-J., San-Félix A., Balzarini J., and De Clercq E. J. Med. Chem. 35 (1992) 2721-2727
6. Pérez-Pérez M.-J., San-Félix A., Camarasa M.-J., Balzarini J., and De Clercq E. Tetrahedron Lett. 33 (1992) 3029-3032
7. Camarasa M.-J., San-Félix A., Velázquez S., Pérez-Pérez M.-J., Gago F., and Balzarini J. Curr. Top. Med. Chem. 4 (2004) 945-963
8. Camarasa, M. J.; Pérez-Pérez, M. J.; Velázquez, S.; San-Félix, A., Alvarez, R.; Ingate, S.; Jimeno, M. L.; De Clercq, E.; Balzarini, J. An overview of TSAO-T derivatives, a 'peculiar' class of HIV-1 specific RT inhibitors. In Antiinfectives. Recent Advances in Chemistry and Structure-Activity Relationships, Bentley, P. H., O'Hanlon, P. J., Eds.; The Royal Society of Chemistry, 1997, Chapter 18, pp 259-268.
9. Pérez-Pérez M.-J., San-Félix A., Balzarini J., De Clercq E., and Camarasa M.-J. J. Med. Chem. 35 (1992) 2988-2995
10. Ingate S., Pérez-Pérez M.J., De Clercq E., Balzarini J., and Camarasa M.J. Antiviral Res. 27 (1995) 281-299
11. Chamorro C., Pérez-Pérez M.J., Rodríguez-Barrios F., Gago F., De Clercq E., Balzarini J., San-Félix A., and Camarasa M.J. Antiviral Res. 50 (2001) 207-222
12. Alvarez R., Jimeno M.L., Gago F., Balzarini J., Perez-Perez M.J., and Camarasa M.J. Antiviral Chem. Chemother. 9 (1998) 333-340
13. Lobatón E., Rodríguez-Barrios F., Gago F., Pérez-Pérez M.J., De Clercq E., Balzarini J., Camarasa M.J., and Velázquez S. J. Med. Chem. 45 (2002) 3934-3945
14. Velázquez S., San-Félix A., Pérez-Pérez M.J., Balzarini J., De Clercq E., and Camarasa M.J. J. Med. Chem. 36 (1993) 3230-3239
15. San-Félix A., Velázquez S., Pérez-Pérez M.J., Balzarini J., De Clercq E., and Camarasa M.J. J. Med. Chem. 37 (1994) 453-460
16. Bonache M.C., Chamorro C., Velázquez S., De Clercq E., Balzarini J., Rodríguez-Barrios F., Gago F., Camarasa M.J., and San-Félix A. J. Med. Chem. 48 (2005) 6653-6660
17. Postel D., Nguyen Van Nhien A., Pillon M., Villa P., and Ronco G. Tetrahedron Lett. 41 (2000) 6403-6406
18. Postel D., Nguyen Van Nhien A., Villa P., and Ronco G. Tetrahedron Lett. 42 (2001) 593-595
19. Postel D., Nguyen Van Nhien A., and Marco J.L. Eur. J. Org. Chem. 19 (2003) 3713-3726
20. Nguyen Van Nhien A., Tomassi C., Len C., Marco-Contelles J., Balzarini J., Pannecouque C., De Clercq E., and Postel D. J. Med. Chem. 48 (2005) 4276-4284
21. Soriano S., Marco-Contelles J., Tomassi C., Nguyen Van Nhien A., and Postel D. J. Chem. Inf. Model. 46 (2006) 1666-1677
22. Gagnieu C.H., Guiller A., and Pacheco H. Carbohydr. Res. 180 (1988) 223-231
23. Gagnieu C.H., Guiller A., and Pacheco H. Carbohydr. Res. 180 (1988) 233-242
24. Domínguez L., Nguyen Van Nhien A., Tomassi C., Len C., Postel D., and Marco-Contelles J. J. Org. Chem. 69 (2004) 843-856
25. Nguyen Van Nhien A., Domínguez L., Tomassi C., Rosario Torres M., Len C., Postel D., and Marco-Contelles J. Tetrahedron 60 (2004) 4709-4727
26. Lobatón E., Rodríguez-Barrios F., Gago F., Pérez-Pérez M.-J., De Clercq E., Balzarini J., Camarasa M.-J., and Velázquez S. J. Med. Chem. 45 (2002) 3934-3945