Synthesis of 4-anilino-1H-pyrazolo [3,4-b] pyridine derivatives and their in vitro antiviral activities

Journal of the Brazilian Chemical Society

Volumn 7, Issue 5, 1996, Pages 273-277

  Bernardino, A M R ^a   Ferreira, V F ^a   Fontoura, G A T ^a   Frugulhetti, I C P P ^a   Lee, M Y ^b   Romeiro, G A ^a   Souza, M C B ^a   Sa P M ^a  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^b UNIVERSITY OF MIAMI   (United States)

Author keywords

Antiviral; Pyrazolopyridine; Reverse transcriptase

Indexed keywords

EID: 0030485736     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.5935/0103-5053.19960055     Document Type: Article

References (23)

1. Huryn, D.M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
2. Périgaud, C.; Gosselin, G.; Imbach, J.L. Nucleosides & Nucleotides 1992, 11, 903.
3. Mansuri, M.M.; Hitchcock, M.J.M. Chemtech 1992, 564.
4. Parker, K.A.; Cobum, C.A. J. Org. Chem. 1991, 56, 4600.
5. Hizi, A.; Hughes, S.H.; Shaharabany, M. Virology 1990, 175, 575.
6. Yarchoan, R.; Mitsuya, H.; Myers, C.E.; Broder, S. N. Engl. J. Med. 1989, 321, 726.
7. De Clercq, E. J. Med. Chem. 1986, 29, 1561.
8. Bazin, H.; Chattopahyaya, J.; Datema, R.; Ericson, A.C.; Gilljam, G.; Johansson, N.G.; Hansen, J.; Koshida, R.; Öberg, B.; Moellina, K.; Rjemaud, G.; Wu, J.C.; Stening, G.; Vrang, L.; Wahren, B.W. Biochem. Pharmacol. 1989, 38, 109.
9. Carrol, S.S.; Olsen, D.B.; Bennett, C.D.; Gotlib, L.; Ruo, L.C.; Graham, D.J.; Condra, J.H.; Stern, A.N.; Shafer, J.A. J. Biol. Chem. 1993, 268, 276.
10. Hardy, C.R.; Adv. Heterocycl. Chem. 1984, 36, 343.
11. Khan, M.A.; Teo, H.C.; Loynch, B.M.; Pedrotti, F. Can. J. Chem. 1988, 66, 420.
12. Bare, T.M.; McLaren, C.D.; Campbell, J.B.; Firor, J.W.; Resch, J.F.; Walters, C.P.; Salamana, A.I.; Meiners, B.A.; Patel, J.B.; J. Med Chem. 1989, 32, 2561.
13. Puar, M.S.; Funke, P.T.; Cohen, A.I. J. Pharm. Sci. 1978, 67, 850.
14. Ferreira, V.F.; Bernardino, A.M.R.; Souza, A.M.R.; Alves, G.A.; Matta, A.D., Oliveira; M.R.P. Nucleosides & Nucleotides 1996, 15, 889.
15. Khan, M.A.; Pedrotti, F. Monatsh. Chem. 1982, 113, 123.
16. Hoehn, H.; Denzel, T.; Jannsen, W. J. Heterocycl. Chem. 1972, 9, 235.
17. Elemental analysis of compounds 8a-e (%, calcd./found) for C, H and N; 8a: C 70.95/71.10; H 5.41/5.58; N 15.04/15.29; 8b: C 71.48/71.18; H 5.74/5.74; N 14.50/14.21; 8c: C 71.48/71.19; H 5.74/5.86; N 14.50/14.20; 8d: C 64.94/64.93; H 4.70/4.68; N 13.77/13.75; 8e: C 63.29/63.38; H 4.59/4.67; N 16.78/16.63.
18. 6) 9a, 1.72 (3H), 7.06-8.28 (10H), 9.01 (1H), 10.52-10.66 (2H); 9b, 1.60 (3H), 7.04-8.30 (9H), 9.01 (1H), 10.42-10.56 (2H); 9c, 1.72 (3H), 7.00-8.30 (9H), 9.02 (1H), 10.50-10.68 (2H); 9d, 1.74 (3H), 7.14-8.28 (9H), 9.04 (1H), 10.56-10.68 (2H); 9e, 1.74 (3H), 7.01-8.28 (9H), 9.04 (1H), 10.54-10.66 (2H).
19. Hizi, A.; McGill, C. Hughes, S.H.; Proc. Nat. Acad. Sci. USA, 1988, 55, 1218.
20. Lee, M.Y.W.T.; Jiang, Y.; Zhang, S; Jand Toomey, N.L. J. Biol. Chem. 1991, 266, 2423.
21. Lee, M.Y.W.T.; Tan, C.K.; Downey, K M.; So, A.G. Biochemistry 1984, 23, 1906.
22. Lee, M.Y.W.T.; Toomey, N.L. Biochemistry 1987, 26, 1076.
23. Ferreira, V.F. Química Nova 1992, 15, 348.