Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 14, 2007, Pages 3872-3876

  Magedov, Igor V ^a,b   Manpadi, Madhuri ^c   Evdokimov, Nikolai M ^a   Elias, Eerik M ^c   Rozhkova, Elena ^a   Ogasawara, Marcia A ^c   Bettale, Jennifer D ^c   Przheval'skii, Nikolai M ^a   Rogelj, Snezna ^c   Kornienko, Alexander ^c  

^a RUSSIAN STATE AGRARIAN UNIVERSITY   (Russian Federation)

^b Intelbioscan Ltd   (Russian Federation)

^c NEW MEXICO INSTITUTE OF MINING AND TECHNOLOGY   (United States)

Author keywords

Apoptosis; Cytotoxicity; Heterocycles; Multicomponent synthesis

Indexed keywords

4 HYDROXY 1,6 DIMETHYLPYRIDIN 2(1H) ONE; BENZALDEHYDE DERIVATIVE; MALONONITRILE; PYRANO[3,2 C]PYRIDONE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; HELA CELL; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL LINE; MITOSIS INHIBITION; ONE STEP MULTICOMPONENT SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

APOPTOSIS; CELL PROLIFERATION; HUMANS; JURKAT CELLS; PYRIDONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34250334153     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.05.004     Document Type: Article

References (36)

1. See. Gorobets N.Y., Yousefi B.H., Belaj F., and Kappe C.O. Tetrahedron 60 (2004) 8633 and references cited therein
2. Pettit G.R., Du J., Pettit R.K., Richert L.A., Hogan F., Mukku J.V.R.V., and Hoard M.S. J. Nat. Prod. 69 (2006) 804
3. Saag M.S., Emini E.A., Laskin O.L., Douglas J., Lapidus W.I., Schleif W.A., Whitley R.J., Hildebrand C., Byrnes V.W., Kappes J.C., Anderson K.W., Massari F.E., and Shaw G.M. N. Engl. J. Med. 329 (1993) 1065
4. Hasegawa G.R. Clin. Pharm. 5 (1986) 201
5. Choudhari B.P., and Mulwad V.V. Indian J. Chem. Sect. B-Org. Chem. Incl. Med. Chem. 42 (2003) 2080
6. Balasubramanian C., Sekar M., and Mohan P.S. Indian J. Chem. Sect. B-Org. Chem. Incl. Med. Chem. 35 (1996) 1225
7. Elagamey A.G.A.E., Sawellim S.Z., El-Taweel F.M.A., and Elnagdi M.H. Coll. Czech. Chem. Commun. 53 (1988) 1534
8. El-Taweel F.M.A., Sofan M.A., Mashaly M.A., Hanna M.A., and Elagamey A.A. Pharmazie 45 (1990) 671
9. Sowellim S.Z.A., El-Taweel F.M.A.A., and Elagamey A.G.A. Bull. Soc. Chim. Fr. 133 (1996) 229
10. El-Nabi H.A.A. Pharmazie 52 (1997) 28
11. Mekheimer R.A., Mohamed N.H., and Sadek K.U. Bull. Chem. Soc. Jpn. 70 (1997) 1625
12. Dodia N., and Shah A. Indian J. Heterocycl. Chem. 10 (2000) 155
13. Stoyanov E.V., Ivanov I.C., and Heber D. Molecules 5 (2000) 19
14. Dodia N., and Shah A. Heterocycl. Commun. 7 (2001) 289
15. Stadlbauer W., Badawey E.S., Hojas G., Roschger P., and Kappe T. Molecules 6 (2001) 338
16. Mulwad V.V., and Lohar M.V. Indian J. Heterocycl. Chem. 12 (2002) 57
17. Rodinovskaya L.A., Shestopalov A.M., and Gromova A.V. Russ. Chem. Bull., Int. Ed. 52 (2003) 2185
18. Rodinovskaya L.A., Shestopalov A.M., Shestopalov A.A., and Litvinov V.P. Russ. Chem. Bull., Int. Ed. 54 (2005) 992
19. El-Taweel F.M.A.A. J. Heterocyclic Chem. 42 (2005) 943
20. Rodinovskaya L.A., Shestopalov A.M., Gromova A.V., and Shestopalov A.A. Synthesis (2006) 2357
21. Kemnitzer W., Kasibhatla S., Jiang S., Zhang H., Zhao J., Jia S., Xu L., Crogan-Grundy C., Denis R., Barriault N., Vaillancourt L., Charron S., Dodd J., Attardo G., Labrecque D., Lamothe S., Gourdeau H., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 15 (2005) 4745
22. Gourdeau H., Leblond L., Hamelin B., Desputeau C., Dong K., Kianicka I., Custeau D., Boudreau C., Geerts L., Cai S.-X., Drewe J., Labrecque D., Kasibhatla S., and Tseng B. Mol. Cancer Ther. 3 (2004) 1375
23. Kasibhatla S., Gourdeau H., Meerovitch K., Drewe J., Reddy S., Qiu L., Zhang H., Bergeron F., Bouffard D., Yang Q., Herich J., Lamothe S., Cai S.X., and Tseng B. Mol. Cancer Ther. 3 (2004) 1365
24. Kemnitzer W., Drewe J., Jiang S., Zhang H., Wang Y., Zhao J., Jia S., Herich J., Labreque D., Storer R., Meerovitch K., Bouffard D., Rej R., Denis R., Blais C., Lamothe S., Attardo G., Gourdeau H., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 47 (2004) 6299
25. Cai, S. X.; Jiang, S.; Kemnitzer, W. E.; Zhang, H.; Attardo, G.; Denis, R. PCT Int. Appl. WO 2003097806 A2 20031127, 2004.
26. Cai, S. X.; Jiang, S.; Attardo, G.; Denis, R.; Storer, R.; Rej, R. PCT Int. Appl. WO 2003096982 A2 20031127, 2003.
27. Cai, S. X.; Zhang, H.; Jiang, S.; Storer, R. PCT Int. Appl. WO 2002092594 A1 20021121, 2002.
28. Cai, S. X.; Xu, L.; Storer, R.; Attardo, G. PCT Int. Appl. WO 2002092083 A1 20021121, 2002.
29. Cai, S. X.; Zhang, H.; Kemmitzer, W. E.; Jiang, S.; Drewe, J. A.; Storer, R. PCT Int. Appl. WO 2002092076 A1 20021121, 2002.
30. Drewe, J. A.; Cai, S. X.; Wang, Y. PCT Int. Appl. WO 2001034591 A2 20010517, 2001.
31. 2) chromenes C (log P ∼ 3.5-4.5).
32. Castillo S., Ouadahi H., and Herault V. Bull. Soc. Chim. Fr. (1982) 257
33. 3 as a catalyst:. Wang X.S., Zeng Z.S., Shi D.Q., Wei X.Y., and Zong Z.M. Synth. Commun. 34 (2004) 3021
34. 1H NMR analysis.
35. +) 440.0222, found 440.0223.
36. Mosmann T. J. Immunol. Methods 65 (1983) 55