Analogues of cytostatic, fused indazolinones: Synthesis, conformational analysis and cytostatic activity against HeLa cells of some 1-substituted indazolols, 2-substituted indazolinones, and related compounds

Liebigs Annales

Volumn , Issue 5, 1996, Pages 683-691

  Arán, Vicente J ^a   Flores, María ^a   Muñoz, Pilar ^a   Páez, Juan A ^a   Sánchez Verdú, Prado ^a,b   Stud, Manfred ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

3 Alkoxyindazoles, 1 substituted; Conformational analysis; Cytostatic activity; Indazol 3 ols, 1 substituted; Indazolin 3 ones, 2 substituted and 1,2 disubstituted

Indexed keywords

EID: 33748989266     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960507     Document Type: Article

References (28)

1. V. J. Arán, J. L. Asensio, J. R. Ruiz, M. Stud, J. Chem. Soc., Perkin Trans. 1 1993, 1119-1127.
2. J. R. Ruiz, V. J. Arán, J. L. Asensio, M. Flores, M. Stud, Liebigs Ann. Chem. 1994, 679-684.
3. V. J. Arán, M. Flores, P. Muñoz, J. R. Ruiz, P. Sánchez-Verdú, M. Stud, Liebigs Ann. 1995, 817-824.
4. A. Burger, Prog. Drug. Res. 1991, 37, 287-371.
5. E. C. Dodds, L. Goldberg, W. Lawson, R. Robinson, Nature (London) 1938, 41, 247-248.
6. H. J. Schaeffer, L. Beauchamp, P. de Miranda, G. B. Elion, D. J. Bauer, P. Collins, Nature (London) 1978, 272, 583-585.
7. L. Baiocchi, G. Corsi, G. Palazzo, Synthesis 1978, 633-648.
8. J. March, Advanced Organic Chemistry - Reactions, Mechanisms, and Structure, 4th ed., John Wiley & Sons, New York, 1992, p. 75-79.
9. E. J. Milner-White, B. M. Ross, R. Ismail, K. Belhadj-Mostefa, R. Poet, J. Mol. Biol. 1988, 204, 777-782.
10. E. J. Milner-White, J. Mol. Biol. 1990, 216, 385-397.
11. P. Ballesteros, J. Elguero, R. M. Claramunt, R. Faure, M. C. Foces-Foces, F. H. Cano, A. Rousseau, J. Chem. Soc., Perkin Trans. 2 1986, 1677-1681.
12. D. E. Goldberg, W. C. Fernelius, J. Phys. Chem. 1959, 63, 1246-1249.
13. W. H. Gray, J. Chem. Soc. 1925, 1150-1158.
14. J. Schmutz, F. Hunziker, W. Michaelis, Helv. Chim.Acta 1964, 47, 1986-1995.
15. S. D. Wyrick, P. J. Voorstad, G. Cocolas, I. H. Hall, J. Med. Chem. 1984, 27, 768-772.
16. P. Bruneau, C. Delvare, M. P. Edwards, R. M. McMillan, J. Med. Chem. 1991, 34, 1028-1036.
17. D. R. Buckle, C. J. M. Rockell, J. Chem. Soc., Perkin Trans. 1 1982, 627-630.
18. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
19. G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer Verlag, Berlin & Heidelberg, 1991, p. 29.
20. K. Pfannstiel, J. Janecke, Ber. Dtsch. Chem. Ges. 1942, 75, 1096-1107.
21. G.-A. Holmberg, Acta Chem. Scand. 1955, 9, 555-561.
22. M. C. Hart, A. D. Hirschfelder, J. Am. Chem. Soc. 1921, 43, 1688-1693.
23. INSIGHT II (2.2.0 version), Discover (2.9/3.1 version), Biosym Technologies, San Diego, USA, 1992.
24. P. Dauber-Osguthorpe, V. A. Roberts, D. J. Osguthorpe, J. Wolff, M. Genest, A. T. Hagler, Proteins: Structure, Function and Genetics, 1988, 4, 31-47.
25. J. J. P. Stewart, MOPAC 6.0, QCPE programm 455, Indiana University, Bloomington, IN 47405, USA, 1990.
26. R. I. Geran, N. H. Greenberg, M. M. Macdonald, A. M. Schumacher, B. J. Abbott, Cancer Chemother. Rep. Part 3 1972, 3(2), 1-103.
27. L. Baiocchi, G. Corsi, G. Palazzo, Ann. Chim. (Rome) 1965, 55, 116-125.
28. G. Palazzo, G. Corsi, L. Baiocchi, B. Silvestrini, J. Med. Chem. 1966, 9, 38-41.