Olcay BEKİRCAN, Bahittin KAHVECİ, Murat KÜÇÜK

Synthesis and Anticancer Evaluation of Some New Unsymmetrical 3,5-Diaryl-4H-1,2,4-Triazole Derivatives

A series of 4-arylidenamino-4H-1,2,4-triazole derivatives (3-11) were synthesized from the treatment of 4-amino-4H-1,2,4-triazoles (2) with certain aldehydes. Compounds 3-11 were reduced with NaBH4 to afford the corresponding 4-arylmethylenamino-4H-1,2,4-triazoles (12-20). Compounds 1-10 and 12-19 were characterized by elemental analyses and 1H NMR, 13C NMR, IR and UV spectral data. Compounds 11 and 20 were characterized by 1H NMR, 13C NMR, IR and mass spectral data. Compounds 14, 16, 17, and 18 were tested for anticancer activities. Compound 17, chosen for its higher anticancer activity in the preliminary tests with the cancer cell lines of MCF7, NCI-H460, and SF-268, exhibited remarkable anticancer potential in screening tests with 60 human cancer cell lines.

Anahtar Kelimeler:

4H-1, 2, 4-Triazoles, 4-Amino-4H-1, 2, 4-triazoles, 4-Arylidenamino-4H-1, 2, 4-triazoles, 4-Arylmethylenamino-4H-1, 2, 4-triazoles, Synthesis, Anticancer activity

Synthesis and Anticancer Evaluation of Some New Unsymmetrical 3,5-Diaryl-4H-1,2,4-Triazole Derivatives

Keywords:

4H-1, 2, 4-Triazoles, 4-Amino-4H-1, 2, 4-triazoles, 4-Arylidenamino-4H-1, 2, 4-triazoles, 4-Arylmethylenamino-4H-1, 2, 4-triazoles, Synthesis, Anticancer activity,

PDF

___

O.G. Todoulou, A.E. Papadaki-Valiraki, S. Ikeda and E.D. Clercq, Eur. J. Med. Chem. 29, 611-620 (1994)
˙I. K¨u¸c¨ukg¨uzel, S¸.G. K¨u¸c¨ukg¨uzel, S. Rollas, G. ¨Ot¨uk-Sanı¸s, O. ¨Ozdemir, ˙I. Bayrak, T. Altu˘g and J.P. Stables, Il Farmaco 59, 893-901 (2004).
S. Rollas, N. Kalyoncuoglu, D. Sur-Altiner and Y. Yegenoglu, Pharmazie 48, 308-309 (1993).
F. Malbec, R. Milcent and P. Vicart, J. Heterocycl. Chem. 21, 1769-1775 (1984).
B. Modzelewska and J. Kalabun, Pharmazie 54, 503 (1999).
N. G¨ulerman, S. Rollas, M. Kiraz, A.C. Ekinci and A. Vidin, Il Farmaco 52, 691- 695 (1997).
A.A. ˙Ikizler, A. ˙Ikizler, M. Serdar and N. Yıldırım, Acta Pol. Pharm. Drug Res. 54, 363-369 (1997).
O. Bekircan and N. G¨umr¨uk¸c¨uoglu, Indian J. Chem. 44B, 2107-2113 (2005).
B. Kahveci and A.A. ˙Ikizler, Acta Pol. Pharm. Drug Res. 57, 119-124 (2000).
N. Demirbas, R. Ugurluoglu and A. Demirbas, Bioorg. Med. Chem. 10, 3717-3723 (2002).
B. Kahveci, O. Bekircan, M. Serdar and A.A. Ikizler, Indian J. Chem. 42B, 1527-1530 (2003).
N. Demirba¸s, R. U˘gurluo˘glu, A. Demirbas and K. Sancak, Eur. J. Med. Chem. 39, 793 (2004).
N. Demirba¸s and R. U˘gurluo˘glu, Turk. J. Chem. 28, 679-690 (2004).
M.P. Grammaticakis and M.G. Champetier, C.R. Acad. Sci. Paris 271, 940-943 (1970).
R. Milcent and C. Redeuilh, J. Heterocycl. Chem. 14, 53-58 (1977).
Z. Hovii, T. Sakai and T. Inoi, J. Pharm. Soc. Japan 75, 1161-1167 (1955).
J.H. Billman and A.C. Diesing, J. Org. Chem. 22, 1068-1074 (1957).
A.R. Katritzky and K.S. Laurenzo, J. Org. Chem. 53, 3978-3982 (1988).
B. Kahveci and A.A. ˙Ikizler, Turk. J. Chem. 24, 343-350 (2000).
G.D. Gray and E. Wickstrom, Biotechniques 21, 780-782 (1996).
M.C. Alley, D.A. Scudiero, P.A. Monks, M. L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker and M.R. Boyd, Cancer Res. 48, 589-601 (1988).
M.R. Grever, S.A. Schepartz and B.A. Chabner, Semin. Oncol. 19, 622-638 (1992).
M.R. Boyd and K.D. Paull, Drug Develop. Res. 34, 91-109 (1995).
W. Zielinski and W. Czardybon, Chem. Heterocycl. Comp. 37, 1107-1110 (2001).
M. Traisnel, B. Mernari and H. Elattari, J. Heterocycl. Chem. 36, 149-152 (1999).
S. Brooker, Coordin. Chem. Rev. 241, 119-132 (2003).
Y. Ikemi, N. Hayashi, A. Kakehi and K. Matsumoto, Heterocycl. Commun. 8, 439-442 (2002).
H. Koshima, M. Hamada, M. Tani, S. Iwasaki and F. Sato, Heterocycles 57, 2145-2148 (2002).
F. Bentiss, M. Lagrenee, B. Elmehdi, B. Mernari, M. Traisnel and H. Vezin, Corrosion 58, 399-407 (2002).
F. Bentiss, M. Lagrenee, H. Vezin, M. Bouanis and B. Mernari, J. Heterocycl. Chem 39, 93-96 (2002).
F. Bentiss, M. Lagrenee and D. Barbry, Tetrahedron Lett. 41, 1539-1541 (2000).
F. Bentiss, M. Lagrenee, M. Traisnel, B. Mernari and H. Elattari, J. Appl. Electrochem. 29, 1073-1078 (1999).
B. Mernari, H. Elattari, M. Traisnel, F. Bentiss and M. Lagrenee, Corros. Sci. 40, 391-399 (1998).