Pyrimido[4,5-c]quinolin-1(2H)-ones as a novel class of antimitotic agents: Synthesis and in vitro cytotoxic activity

European Journal of Medicinal Chemistry

Volumn 42, Issue 3, 2007, Pages 344-350

  Metwally, Kamel ^a   Pratsinis, Harris ^b   Kletsas, Dimitris ^b  

^a Zagazig University   (Egypt)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

Antimitotic; Cytotoxic agents; Pyrimido 4,5 c quinolin 1(2H) ones

Indexed keywords

2 AMINO 3,5 BIS(4 CHLOROPHENYL)PYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 BROMOPHENYL) 3 (4 CHLOROPHENYL)PYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 BROMOPHENYL) 3 METHYLPYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 BROMOPHENYL) 3 PHENYLPYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 BROMOPHENYL) 9 CHLORO 3 (4 CHLOROPHENYL)PYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 BROMOPHENYL) 9 CHLORO 3 PHENYLPYRIMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 CHLOROPHENYL) 3 METHYLPYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 5 (4 CHLOROPHENYL) 3 PHENYLPYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 9 CHLORO 3,5 BIS(4 CHLOROPHENYL)PYRIMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 9 CHLORO 5 (4 CHLOROPHENYL) 3 METHYLPYRAMIDO[4,5 C]QUINOLIN 1(2H) ONE; 2 AMINO 9 CHLORO 5 (4 CHLOROPHENYL) 3 PHENYLPYRIMIDO[4,5 C]QUINOLIN 1(2H) ONE; ANTIMITOTIC AGENT; HALOGEN; LACTONE DERIVATIVE; PACLITAXEL; PHENYL GROUP; QUINOLINE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; COLON ADENOCARCINOMA; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IN VITRO STUDY; LUNG SARCOMA; PROTEIN POLYMERIZATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANTIMITOTIC AGENTS; ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PYRIMIDINES; QUINOLONES; SOLVENTS; SPECTROPHOTOMETRY, INFRARED; TUBULIN; TUBULIN MODULATORS;

EID: 33847368131     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2006.10.008     Document Type: Article

References (35)

1. Amos L., and Klug A. J. Cell Sci. 14 (1974) 523-549
2. McIntosh J., Grishchunk E., and West R. Annu. Rev. Cell Dev. Biol. 18 (2002) 193-219
3. Desai A., and Mitchison T. Annu. Rev. Cell Dev. Biol. 13 (1997) 83-117
4. Wilson L., and Jordan M. Chem. Biol. 2 (1995) 569-573
5. Jordan M., Wendell K., Gardiner S., Derry W., Copp H., and Wilson L. Cancer Res. 56 (1996) 816-825
6. Chen J., Yang C., Cammer M., and Horwitz S. Cancer Res. 63 (2003) 7891-7899
7. Zhou J., Panda D., Landen J., Wilson L., and Joshi H. J. Biol. Chem. 277 (2002) 17200-17208
8. Yvon A., Wadsworth P., and Jordan M. Mol. Biol. Cell 10 (1999) 947-959
9. Derry W., Wilson L., and Jordan M. Biochemistry 34 (1995) 2203-2211
10. Gonclaves A., Braguer D., Kamath K., Martello L., Briand C., Horwitz S., Wilson L., and Jordan M. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 11737-11741
11. Zhou J., and Giannakakou P. Curr. Med. Chem. 5 (2005) 65-71
12. Ambudkar S., Dey S., Hrycyna C., Ramachandra M., Pastan I., and Gottesman M. Annu. Rev. Pharmacol. Toxicol. 39 (1999) 361-398
13. Rowinsky E. Annu. Rev. Med. 48 (1997) 353-374
14. Goa K., and Faulds D. Drugs Aging 5 (1994) 200-234
15. Lai Y., Huang L., Lee K., Xiao Z., Bastow K., Yamori T., and Kuo S. Bioorg. Med. Chem. 13 (2005) 265-275
16. Kuo S., Lee H., Juang J., Lin Y., Wu T., Chang J., Lednicer D., Paull K., Lin C., Hamel E., and Lee K. J. Med. Chem. 36 (1993) 1146-1156
17. Li L., Wang H., Kuo S., Wu T., Mauger A., Lin C., Hamel E., and Lee K. J. Med. Chem. 37 (1994) 3400
18. Ferlin M., Chiarelotto G., Gasparotto V., Via L., Pezzi V., Barzon L., Palu G., and Castagliuolo I. J. Med. Chem. 48 (2005) 3417-3427
19. Li L., Wang H., Kuo S., Wu T., Lednicer D., Lin C., Hamel E., and Lee K. J. Med. Chem. 37 (1994) 1126-1135
20. Xia Y., Yang Z., Xia P., Bastow K., Tachibana Y., Kuo S., Hamel E., Hackl T., and Lee K. J. Med. Chem. 41 (1998) 1155-1162
21. Xia Y., Yang Z., Xia P., Hackl T., Hamel E., Mauger A., Wu J., and Lee K. J. Med. Chem. 44 (2001) 3932-3936
22. Lee K., Tagahara K., Suzuki H., Wu R., Haruna M., Hall I., Huang H., Ito K., Iida T., and Lai J. J. Nat. Prod. 44 (1981) 830-835
23. Shi Q., Chen K., and Li L. J. Nat. Prod. 58 (1995) 475-482
24. Zhao Y., Chen Y., Chang F., and Tzeng C. Eur. J. Med. Chem. 40 (2005) 792-797
25. Chen Y., Huang C., Huang Z., Tseng C., Chang F., Yang S., Lin S., and Tzeng C. Bioorg. Med. Chem. 14 (2006) 3098-3105
26. Peczynska-Czoch W., Pognan F., Kaczmarek L., and Boratynski J. J. Med. Chem. 37 (1994) 3503-3510
27. Chen Y., Hung H., Lu C., Li K., and Tzeng C. Bioorg. Med. Chem. 12 (2004) 6539-6546
28. Chen Y., Chung C., Chen I., Chen P., and Jeng H. Bioorg. Med. Chem. 10 (2002) 2705-2712
29. Katoen-Chackal S., Facompre M., Houssin R., Pommery N., Goossens J., Colson P., Bailly C., and Henichart J. J. Med. Chem. 47 (2004) 3665-3673
30. J. Poletto, N. Westwood, D. Powell, N. Valley Cottage, D. Boschelli, M. Novi, U.S. patent, 4,968,702, 1990.
31. Pfitzinger W. J. Prakt. Chem. 33 (1886) 100-105
32. Chang J., Chang C., Kuo C., Chen L., Wein Y., and Kuo Y. Mol. Pharmacol. 65 (2004) 77-84
33. Denizot F., and Lang R. J. Immunol. Methods 89 (1986) 271-277
34. Kostakis I., Tenta R., Pouli N., Marakos P., Skaltsounis A., Pratsinis H., and Kletsas D. Bioorg. Med. Chem. Lett. 15 (2005) 5057-5060
35. Blagosklonny M., Schulte T., Nguyen P., Mimnaugh E., Trepel J., and Neckers L. Cancer Res. 55 (1995) 4623-4626