Synthesis and antitumor activity of novel 2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives

European Journal of Medicinal Chemistry

Volumn 37, Issue 9, 2002, Pages 709-720

  Brzozowski, Z ^a   Saczewski F ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

2 Amino 4 (3,5,5 trimethyl 2 pyrazolino) 1,3,5 triazine derivatives; Antitumor effect; Structures; Synthesis

Indexed keywords

2 (2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] 3 (5 NITRO 2 THIENYL)ACRYLONITRILE; 2 [2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] 3 (2 HYDROXY 4 METHOXYPHENYL)ACRYLONITRILE; 2 [2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] 3 (2 HYDROXYPHENYL)ACRYLONITRILE; 2 [2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] 3 (4 DIETHYLAMINOPHENYL)ACRYLONITRILE; 2 [2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] 3 (4H 4 OXOCHROMEN 3 YL)ACRYLONITRILE; 2 [AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZIN 6 YL] 3 (5 NITRO 2 FURYL)ACRYLONITRILE; 2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 6 (2 IMINO 2H CHROMEN 3 YL) 1,3,5 TRIAZINE; 2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 6 (2 IMINO 7 METHOXY 2H CHROMEN 3 YL) 1,3,5 TRIAZINE; 2 AMINO 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 6 (2 SULFAMOYLPHENYL) 1,3,5 TRIAZINE; 2 AMINO 6 (PHENYLSULFONYLMETHYL) 4 (3,5,5 TRIMETHYL 2 PYRAZOLINO) 1,3,5 TRIAZINE; ANTINEOPLASTIC AGENT; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAIN CANCER; BREAST CANCER; CELL LINE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA; TUMOR CELL;

ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES; TUMOR CELLS, CULTURED;

EID: 0036753651     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(02)01379-X     Document Type: Article

References (24)

1. Hayoshi S., Furakawa M., Fujino Y., Yoshimatsu S. Chem. Pharm. Bull. 17:1969;329-334.
2. Stivens M.F.G., Bliss E.A., Brown T.B., Mckenzie S.M. Eur. J. Chem.-Chim. Ther. 19:1984;372-379.
3. M. Hitoshi, U. Fusao, PCT Int. Appl. WO 1992 11, Nippon Shinyaku Co Ltd., p. 247; Chem. Abstr. 118 (1993) 38951 d.
4. M. Hitoshi, U. Fusao, PCT Int. Appl. WO 1992 11, Nippon Shinyaku Co Ltd., p. 247; Chem. Abstr. 118 (1993) 38951 d.
5. Mayumi O., Kawahara N., Goto D., Wakabyashi Y., Ushiro S., Yoshida S., Izumi H., Kuwano M., Sato Y. Cancer Res. 56:1966;1512-1516.
6. T. Hori, M. Asamoto, V. Krutovskikh, Y. Iwahori, M. Maeda, H. Toriyama-Baba, N. Takasuka, H. Tsuda, Chemotherapy Division, Nation Cancer Res. Inst., Tokyo, Japan, p. 104; Jpn. Cancer Res. (88) 12; Chem. Abstr. 126 (1997) 194926 v.
7. T. Hori, M. Asamoto, V. Krutovskikh, Y. Iwahori, M. Maeda, H. Toriyama-Baba, N. Takasuka, H. Tsuda, Chemotherapy Division, Nation Cancer Res. Inst., Tokyo, Japan, p. 104; Jpn. Cancer Res. (88) 12; Chem. Abstr. 126 (1997) 194926 v.
8. T. Hori, M. Asamoto, V. Krutovskikh, Y. Iwahori, M. Maeda, H. Toriyama-Baba, N. Takasuka, H. Tsuda, Chemotherapy Division, Nation Cancer Res. Inst., Tokyo, Japan, p. 104; Jpn. Cancer Res. (88) 12; Chem. Abstr. 126 (1997) 194926 v.
9. Brzozowski Z., Sa̧czewski F. Eur. J. Med. Chem. 35:2000;1053-1064.
10. Pilarski B. Liebigs Ann. Chem. 1983;1078-1080.
11. Brzozowski Z., Kamiński Z., Kozakiewicz I., Angielski S., Rogulski J. Acta Pol. Pharm. 36:1979;401-410.
12. O'Callaghan C.N., McMurry B.H., O'Brien J.E., Draper S.M., Wilcock D.J. J. Chem. Soc. Perkin Trans. I. 1996;1067-1071.
13. Profft E., Stuhmer K. Arch. Pharm. 300:1967;1-6.
14. Czerney P., Hartman H. Z. Pharm. 21:1981;408-415.
15. All simulations were carried out in gas-phase using 'Conformer Search' and 'Transition Search' modules with the semiempirical AM1 and the Becke-Perdew non-local density functional model (BP) as implemented in Spartan 5.1 (SGI version from Wavefunction Inc., Irvine, California, USA) molecular modeling package.
16. Boyd M.R. Am. Assoc. Cancer Res. 30:1989;652-665.
17. Monks A., Scudiero D., Skehan P., Shoemaker R., Poull K., Visica D., Hose C., Langley J., Cronise P., Vaigro-Wolf A., Gray-Goodrich M., Cambell H., Mayo J., Boyd M. J. Natl. Cancer Inst. 83:1991;757-766.
18. Weinstein J.N., Myers T.G., O'Connor P.M., Friend S.H., Fornance A.J.Ir., Kohn K.W., Fojo T., Bates S.E., Rubinstein L.V., Anderson N.L., Buolamwini J.K., van Osdol W.W., Monks A.P., Scudiero D.A., Sausville E.A., Zaharevitz D.W., Bunow B., Viswandhan V.N., Johnson G.S., Wittes R.E., Paull K.D. Science. 275:1997;343-349.
19. Gazit A., Osherov N., Giton C., Levitzki A. J. Med. Chem. 39:1996;4905-4911.
20. Gazit A., App H., McMahon G., Chen J., Levitzki A., Bohmer F.F. J. Med. Chem. 39:1996;2170-2177.
21. Dimmock J.R., Kumar P., Quail J.W., Pagazhenthi U., Yang J., Chen M., Reid R.S., Allen T.M., Kao G.Y., Cole S.P.C., Batist G., Balzarini J., De Clercq E. Eur. J. Med. Chem. 30:1995;209-217.
22. Haman N.W., Bassendowski D.L., Wright D.E., Dimmock J.R., Noble L.M. J. Pharm. Sci. 67:1978;1539-1542.
23. Wattenberg L.W., Coccia J.B., Galhaith A.R. Cancer Lett. 83:1983;165-169.
24. Dimmock J.R., Raghaven S.K., Logan B.M., Bigam G.E. Eur. J. Med. Chem. 18:1983;248-254.