Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 2, 2008, Pages 881-889

  Farag, Ahmad M ^a   Mayhoub, Abdelrahman S ^b   Barakat, Saber E ^b   Bayomi, Ashraf H ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b Al Azhar University   (Egypt)

Author keywords

1,3 Dipolar cycloaddition; Antitumor activity; Antitumor agent; Cytotoxicity; Dimethylformamide dimethylacetal (DMF DMA); Enaminones; N Phenylpyrazoles; Nitrilimines; Phenylcarbamoyl 1H pyrazole; Regioselective synthesis; Structure activity relationship (SAR)

Indexed keywords

1,3 DIPHENYL 4 [(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYLPYRAZOL 4 YL)CARBONYL] 1H PYRAZOLE; 2 (2 PHENYLHYDRAZONO) 2 CHLORO N PHENYLACETAMIDE; 3 ACETYL 1 (3 METHYLPHENYL) 4 [(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL)PYRAZOL 4 YL]CARBONYLPYRAZOLE; 3 ACETYL 1 (4 BROMOPHENYL) 4 [(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL)PYRAZOL 4 YL]CARBONYLPYRAZOLE; 3 ACETYL 1 (4 METHYLPHENYL) 4 [(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL)PYRAZOL 4 YL]CARBONYLPYRAZOLE; 3 ACETYL 1 PHENYL 4 [(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL) 1H PYRAZOL 4 YL]CARBONYLPYRAZOLE; 4 [(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL PYRAZOL 4 YL)CARBONYL] 1 PHENYL 3 PHENYLCARBAMOYL 1H PYRAZOLE; 4 [3 (DIMETHYLAMINO)ACRYLOYL] 5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL 1H PYRAZOLE; 4 ACETYL 5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL 1H PYRAZOLE; ACETAL DERIVATIVE; ACETAMIDE DERIVATIVE; ALKANE DERIVATIVE; ANTINEOPLASTIC AGENT; DIHYDROPYRAZOLE; DIMETHYLACETAL; DOXORUBICIN; ETHOXIDE SODIUM; ETHYL 1 (4 BROMOPHENYL) 4 [4[(5 METHYL 1 PHENYL 3 PHENYLCARBAMO YL) 1H PYRAZOLYL]CARBONYL] PYRAZOLE 3 CARBOXYLATE; ETHYL 1 ARYL 4 [4[(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL) 1H PYRAZOLYL]CARBONYL] 1 PHENYLPYRAZOLE 3 CARBOXYLATE; ETHYL 4 [4[(5 METHYL 1 PHENYL 3 PHENYLCARBAMOYL) 1H PYRAZOLYL]CARBONYL] 1 (4 NITROPHENYL) PYRAZOLE 3 CARBOXYLATE; N,N DIMETHYLFORMAMIDE; OXIDE; PENTAN 2,4 DIONE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG SCREENING; DRUG SYNTHESIS; EHRLICH ASCITES TUMOR CELL;

ANTINEOPLASTIC AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DOXORUBICIN; DRUG SCREENING ASSAYS, ANTITUMOR; MOLECULAR STRUCTURE; PYRAZOLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 38749095499     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.015     Document Type: Article

References (36)

1. Abdel-Gawad S.M., Abdel-Aziem A., and Ghorab M.M. Phosphorus Sulfur Silicon 178 (2003) 1795
2. Maekawa, T.; Hara, R.; Odaka, H.; Kimura, H.; Mizufune, H.; Fukatsu, K. PCT Int. Appl. WO 03 99,793. [Chem.Abstr., 2004, 140, 16723h].
3. Mercep, M.; Mesic, M.; Pesic, D. PCT Int. Appl. WO 03 99,822. [Chem.Abstr., 2004, 140, 16724j].
4. Qiao, J. X.; Pinto, D. J.; Orwat, M. J.; Han, W.; Friedrich, S. R. PCT Int. Appl. WO 03 99,276. [Chem.Abstr.,2004, 140, 16722g].
5. Baraldi P.G., Bovero A., Fruttarolo F., Romagnoli R., Tabrizi M.A., Preti D., Varani K., Borea P.A., and Moorman A.R. Bioorg. Med. Chem. 11 (2003) 4161
6. Stamford, A. W.; Wu, Y., PCT Int. Appl. WO 2004 5,262. [Chem.Abstr. 2004, 140, 111411p].
7. Brown, M. L.; Cheung, M.; Dickerson, S. H.; Drewry, D. H.; Lackey, K. E.; Peat, A. J.; Thomson, S. A.; Veal, J. M.; Wilson, J. L. R., PCT Int. Appl. WO 2004 9,596. [Chem.Abstr. 2004, 140, 128436y].
8. Stevensons, T. M.; Lahm, G. P.; Pasteris, R. J., PCT Int. Appl. WO 03 106,427. [Chem.Abstr. 2004, 140, 42172x].
9. Heerding, D. A., PCT Int. Appl. WO 03 103,686. [Chem.Abstr. 2004, 140, 42170v].
10. Cardia M.C., Corda L., Fadda A.M., Maccioni A.M., Maccioni E., and Plumitallo A. Farmaco 53 (1998) 698
11. Mullican M.D., Wilson M.W., Cannor D.T., Kostlan C.R., and Dyer R.D. J. Med. Chem. 36 (1993) 1090
12. Kirkpatrick W.E., Okabe T., Hillyard I., Robins R.K., Dren A.T., and Novinson T. J. Med. Chem. 20 (1977) 387
13. Abadi A.H., Abdel-Haleem E.A., and Hassan G.S. Chem. Pharm. Bull. 51 (2003) 838
14. Furet, P.; Imbach, P.; Ramsey, T. M.; Schlapbach, A.; Scholz, D. and Caravatti, G., PCT Int. Appl. WO 2004 5,282. [Chem. Abstr. 2004, 140, 111424v].
15. Raffa D., Daidone G., Maggio B., Cascioferro S., Plescia F., and Schillaci D. Farmaco 59 (2004) 215
16. Sherif A.F.R. Bioorg. Med. Chem. 14 (2006) 6475
17. Cheung K.-M., Matthews T.P., James K., Rowlands M.G., Boxall K.J., Sharp S.Y., Maloney A., Roe S.M., Prodromou C., Pearl L.H., Aherne G.W., McDonald E., and Workman P. Bioorg. Med. Chem. Lett. 15 (2005) 3338
18. Dymock B.W., Barril X., Brough P.A., Cansfield J.E., Massey A., McDonald E., Hubbard R.E., Surgenor A., Roughley S.D., Webb P., Workman P., Wright L., and Drysdale M.J. J. Med. Chem. 48 (2005) 4212
19. Barril X., Beswick M.C., Collier A., Drysdale M.J., Dymock B.W., Fink A., Grant K., Howes R., Jordan A.M., Massey A., Wayne A.S., Workman J.P., and Wright L. Bioorg. Med. Chem. Lett. 16 (2006) 2543
20. Allan G.M., Bubert C., Vicker N., Smith A., Tutill H.J., Purohit A., Reed M.J., and Potter B.V.L. Molecul. Cell Endocrin. 248 (2006) 204
21. Foglia S., Nieri P., Chicca A., Adinolfi B., Mariotti V., Iacopetti P., Breschi M.C., and Pellegrini S. FEBS Lett. 580 (2006) 1733
22. Yoshida M., Hayakawa I., Hayashi N., Agatsuma T., Oda Y., Tanzawa F., Iwasaki S., Koyama K., Furukawa H., Kurakata S., and Sugano Y. Bioorg. Med. Chem. Lett. 15 (2005) 3328
23. Shaaban R.M., Saleh T.S., Osman F.H., and Farag A.M. J. Heterocycl. Chem. 44 (2007) 177
24. Shaaban R.M., Saleh T.S., and Farag A.M. Heterocycles 71 (2007) 1765
25. Dawood K.M., Farag A.M., and Abdel-Aziz H.A. J. Chin. Chem. Soc. 53 (2006) 873
26. Dawood K.M., Farag A.M., and Abdel-Aziz H.A. Heteroatom Chem. 17 (2005) 621
27. Dawood K.M., Farag A.M., and Abdel-Aziz H.A. J. Chem. Res. (S) (2005) 378
28. Dawood K.M., Ragab E.A., and Farag A.M. J. Chem. Res. (S) 685M (2003) 1151
29. Al-Omran F., Al-Awadi N., Abau El-Khair A., and Elnagdi M.H. Org. Prep. Proced. Int. 29 (1997) 285
30. Shawali A.S., and Osman A. Tetrahedron 27 (1971) 2517
31. Dieckmann W., and Platz O. Chem. Ber. 38 (1906) 2989
32. Hegarty A.F., Cashaman M.P., and Scoti F.L. Chem. Commun. 13 (1971) 884
33. Wolkoff P. Can. J. Chem. 53 (1975) 1333
34. El-Merzabani M.M., El-Aaser A.A., El-Dueini A.K., and EL-Masry A.M. Planta Medica 36 (1979) 87-90
35. Takemoto D.J., Dunford C., and McMurray M.M. Toxicology 20 (1982) 593
36. El-Merzabani M.M., El-Aaser A.A., Attia M.A., El-Dueini A.K., and Ghazal A.M. Planta Medica 36 (1979) 150-155