Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity

European Journal of Medicinal Chemistry

Volumn 44, Issue 4, 2009, Pages 1396-1404

  Havrylyuk, Dmytro ^a   Zimenkovsky, Borys ^a   Vasylenko, Olexandr ^c   Zaprutko, Lucjusz ^b   Gzella, Andrzej ^b   Lesyk, Roman ^a  

^a DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

^b POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^c INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

Anticancer activity; Knoevenagel reaction; Pyrazolines; Thiazolones; X ray study

Indexed keywords

2 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 2 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 4 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 4 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (2 CHLOROBENZYLIDENE) 2 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 5 (3 BROMOBENZYLIDENE) 2 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 5 (4 BROMOBENZYLIDENE) 4 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (4 CHLOROBENZYLIDENE) 2 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 5 (4 CHLOROBENZYLIDENE) 4 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (4 CHLOROBENZYLIDENE) 4 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (4 DIMETHYLAMINOBENZYLIDENE) 2 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 5 (4 DIMETHYLAMINOBENZYLIDENE) 4 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (4 HYDROXY 3,5 DIMETHOXYBENZYLIDENE) 2 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 5 (4 HYDROXYBENZYLIDENE) 4 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (4 METHOXYBENZYLIDENE) 4 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 (4 NITROBENZYLIDENE) 2 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 4(5H) ONE; 5 (4 NITROBENZYLIDENE) 4 [5 (4 METHOXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; 5 BENZYLIDENE 4 [5 (2 HYDROXYPHENYL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 1,3 THIAZOL 2(5H) ONE; PYRAZOLINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAIN CANCER; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HT29; CENTRAL NERVOUS SYSTEM TUMOR; COLON CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; KIDNEY CANCER; KNOEVENAGEL CONDENSATION; LEUKEMIA; LIQUID CHROMATOGRAPHY; LUNG CANCER; MALE; MASS SPECTROMETRY; MELANOMA; NATIONAL HEALTH ORGANIZATION; OVARY CANCER; PROSTATE CANCER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; NEOPLASMS; PYRAZOLES; THIAZOLES;

EID: 61349169067     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.09.032     Document Type: Article

References (33)

1. Lesyk R.B., and Zimenkovsky B.S. Curr. Org. Chem. 8 (2004) 1547-1577
2. Murphy G.I., and Holder J.C. Trends Pharmacol. Sci. 21 (2000) 469-474
3. Charlier C., and Mishaux C. Eur. J. Med. Chem. 38 (2003) 645-659
4. Seno K., Okuno T., Nishi K., Murakami Y., Watanabe F., Matsuura T., Wada M., Fujii Y., Yamada M., Ogawa T., Okada T., Hashizume H., Kii M., Hara S.-i., Hagishita S., Nakamoto S., Yamada K., Chikazawa Y., Ueno M., Teshirogi I., Ono T., and Ohtani M. J. Med. Chem. 43 (2000) 1041-1044
5. Mui Sim M., Bee Ng S., Buss A.D., Crasta S.C., Goh K.L., and Lee S.K. Bioorg. Med. Chem. Lett. 12 (2002) 679-699
6. Cutshall N.S., O'Day C., and Prerzhdo M. Bioorg. Med. Chem. Lett. 15 (2005) 3374-3379
7. Carter P.H., Scherle P.A., Muckelbauer J.A., Voss M.E., Liu R.-Q., Thompson L.A., Tebben A.J., Solomon K.A., Lo Y.C., Li Z., Strzemienski P., Yang G., Falahatpisheh N., Xu M., Wu Z., Farrow N.A., Ramnarayan K., Wang J., Rideout D., Yalamoori V., Domaille P., Underwood D.J., Trzaskos J.M., Friedman S.M., Newton R.C., and Decicco C.P. Proc. Natl. Acad. Sci. U.S.A. 98 21 (2001) 11879-11884
8. Degterev A., Lugovskoy A., Cardone M., Mulley B., Wagner G., Mitchison T., and Yuan J. Nat. Cell Biol. 3 2 (2001) 173-182
9. Dayam R., Aiello F., Deng J., Wu Y., Garofalo A., Chen X., and Neamati N. J. Med. Chem. 49 (2006) 4526-4534
10. Lesyk R., Zimenkovsky B., Atamanyuk D., Jensen F., Kiec-Kononowicz K., and Gzella A. Bioorg. Med. Chem. 14 (2006) 5230-5240
11. Lesyk R., Vladzimirska O., Holota S., Zaprutko L., and Gzella A. Eur. J. Med. Chem. 42 (2007) 641-648
12. Atamanyuk D., Zimenkovsky B., and Lesyk R. J. Sulfur Chem. 29 (2008) 151-162
13. Lesyk R., Zimenkovsky B., Subtelna I., Nektegayev I., and Kazmirchuk G. Acta Polon. Pharm. - Drug Res. 6 (2003) 457-466
14. Özdemir A., Turan-Zitouni G., Kaplancikli Z.A., Revial G., and Güven K. Eur. J. Med. Chem. 42 (2007) 403-409
15. Popov-Pergal K., Cekovic Z., and Pergal M. J. Gen. Chem. USSR 61 (1991) 1958-1962
16. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc., Perkin Trans. 2 (1987) S1-S19
17. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354-1358
18. .
19. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., and Vaigro-Wolff A. J. Nat. Cancer Inst. 83 11 (1991) 757-766
20. Boyd M.R., and Paull K.D. Drug Dev. Res. 34 (1995) 91-109
21. Boyd M.R. In: Teicher B.A. (Ed). Cancer Drug Discovery and Development vol. 2 (1997), Humana Press 23-43
22. Shoemaker R.H. Nat. Rev. Cancer 6 (2006) 813-823
23. Laske R., Schönenberger H., and Holler E. Arch. Pharm. 322 12 (1989) 857-862
24. Kemp A.J., Lyons S.D., and Christopherson R.I. J. Biol. Chem. 261 32 (1986) 14891-14895
25. Org. Synth. 3 (1955) 763
26. Komaritsa I.D., Baranov S.N., and Grishchuk A.P. Khimiya Geterotsiklicheskikh Soedinenii 4 (1967) 664-665
27. Chem. Abstr. 68 (1968) 49495
28. Palaska E., Aytemir V., Uzbay I.T., and Erol D. Eur. J. Med. Chem. 36 (2001) 539-543
29. Kuma Diffraction, Version 8.0.1, KM-4 Software User's Guide, Wrocław, Poland, 1996.
30. North A.C.T., Phillips D.C., and Mathews F.S. Acta Crystallogr. A24 (1968) 351 - 359
31. Sheldrick G.M. SHELXS-97 and SHELXL-97. Release 97-2 (1997), University of Göttingen, Germany
32. Farrugia L.J. J. Appl. Crystallogr. 30 (1997) 565
33. Farrugia L.J. J. Appl. Crystallogr. 32 (1999) 837-838