Synthesis and Antiproliferative Activity in vitro of 1-Phenyl-2-(4-aryl-1,3,4,5-tetrahydropyrido[2,3-b] [1,4]diazepin-2-ylidene)ethanone. Part I.

• Autorzy: Liszkiewicz H. , Kowalska M. W. , Głowiak T. , Wietrzyk J. , Opolski A.
• Języki publikacji: EN

Abstrakty

EN

Reaction of 2,3-diaminopyridine with equimolar amount of benzoylacetone in ethanol solution in the presence of catalytic amounts of acetic acid allowed to obtain 3-(2- amino-pyridin-3-ylamino)-1-phenyl-2-buten-1-one (4) instead of 2-methyl-4-phenyl- 3H-pyrido[2,3-b][1,5]diazepine (3) reported in the literature. Treatment of compound 4 with appropriate aromatic aldehydes: benzaldehyde and substituted benzaldehyde (4- methoxy-, 3,4-dimethoxy-, 3,4,5-trimethoxy-, 3-metyl-4-methoxy-, 3-hydroxy-, 4- diethyloamino-) in methanol solution in the presence of equimolar amount of potassium hydroxide gave 1-phenyl-2-(aryl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]-diazepin-2- ylidene)-ethanones (7-13). Structures of compounds 4 and 7 were determined on a single crystal. Compounds 4 and 7-13 were examined for their antiproliferative activity in vitro against the cells of 7 human cancer cell lines, using SRB orMTTtechnique. Two out of all tested compounds revealed cytotoxic activity in vitro.

Słowa kluczowe

EN

3-(2-amino-pyridin-3-ylamino)-1-phenyl-2-buten-1-one; 1-phenyl-2(aryl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin-2-ylidene)-ethanone; cytotoxicity; crystal structure

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 11
• Strony: 1607--1617
• Opis fizyczny: Bibliogr. 26 poz., rys.

Twórcy

autor

Liszkiewicz H.

• Department of Drugs Technology, Wrocław Medical University, Nankiera 1 Sq., 50-140 Wrocław, Poland

autor

Kowalska M. W.

• Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14 Str., 50-383 Wrocław, Poland

autor

Głowiak T.

• Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14 Str., 50-383 Wrocław, Poland

autor

Wietrzyk J.

• 3Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 R. Weigl Str., 53-114 Wroclaw, Poland

autor

Opolski A.

• 3Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 R. Weigl Str., 53-114 Wroclaw, Poland

Bibliografia

• 1. Littell R. and Allen D.S., J. Med. Chem., 8, 722 (1965).
• 2. Fiakpui C.Y., Arora V.K. and Knaus E.E., J. Heterocycl. Chem. I, 30, 699 (1993).
• 3. Fiakpui C.Y., Phillips O.A., Murthy K.S.K. and Knaus E.E., J. Heterocycl. Chem., 36, 377 (1999).
• 4. Grozingcr K.G., Byrne D.P,, Nummy L.J., Ridges M.D. and Salvagno A., J. Heterocycl. Chem., 37,229 (2000).
• 5. Eberlein W.G., Engel W. W., Trumm litz G., Schmidt G. and Hammer R., J. Med. Chem. ,31,1169(1988).
• 6. Watanabe T., Kakefuda A., Tanaka A., Takizawa K., Hirano S., Shibata H., Yamagiwa Y. and Yanagisawa I., Chem. Pharm. Bull., 46, 53 (1998).
• 7. Karton T., Bradbury B.J., Baumgold J., Paek R. and Jacobson K.A., J. Med. Chem., 24, 2133 (1991).
• 8. Savelli F., Boido A. and Mulé A., Bull. Chim. Farmacéutico - Anno 128, 4, 132 (1989),
• 9. Nawrocka W., Sztuba B,, Opolski A., Wietrzyk J., Kowalska M.W. and Glowiak T,, Arch. Pharm. Pharm. Med. Chem., 334, 1 (2001).
• 10. Nawrocka W., Sztuba B. and Zimecki M., Arch. Pharm. Pharm. Med. Chem., 334, 11 (2001).
• 11. Blache Y., Hichour M., Di Blasi G., Chezal J.M., Viols H., Chavignon O., Teulade J.C. and Chapat J.P., Heterocycles, 51, 1003 (1999).
• 12. Halford J.C. and Fitsch R.M., J. Am. Chem. Soc., 85, 3354 (1963).
• 13. Staab H.A. and Vogtle F., Chem. Ber., 98, 2701 (1963).
• 14. Mannschreck A., Rissmann G., Vogtle F. and Wild D., Chem. Ber., 100, 335 (1967).
• 15. Nawojski A. and Nawrocka W,, Roczn. Chem., 48, 1073 (1974).
• 16. Nawoj ski A., Prace Naukowe Akademii Medycznej we Wrocławiu, Rozprawa habilitacyjna, Akademia Medyczna, Wroclaw, 5(10) (1969).
• 17. LowJ.N., Cobo J., In.suasty B., Insuasty H., Nogueras M. and Sanchez A., Acta Cryst., C58,103 (2002).
• 18. Abramenko B.L., Sergienko VS., Gamovskii A.D. andPorai-Kochitz M. A., Zh. Obsch. Khim., 60,1593 (1990).
• 19. Rodier N., Agafonov V., Dubois P., Mariand M. and Cense J.M., Acta Cryst., C49, 156 (1993).
• 20. Dupont L., Liégeois I.F., Rogister F. and Delagre J., Acta Cryst., C52, 391 (1996).
• 21. Geran R.I., Greenberg N.H., MacDonald M.M., Schumacher A,M. and Abbott B.J., Cancer Chemotherapy Rep., 3, 59 (1972).
• 22. SheldrickG.M., SHELXS97, Program for solution of crystal structures, University of Gottingen ( 1997).
• 23. Sheldrick G.M., SHELXL97, Program for crystal structure refinement, University of Göttingen (1997).
• 24. Sheldrick G.M., SHELXTL-NT V5.1, Bruker AXS (1999).
• 25. Skehan P., Storeng R„ Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S. and Boyol M.R., J. Natl. Cancer. Inst., 82,1107 (1990).
• 26. Opolski A., Kuduk-Jaworka J., Wietrzyk J., Wojdat E„ Waszkiewicz K., Romaniewska A„ Radzikowski C., Anticancer Drugs, 11,363 (2000).