New class of potent antitumor acylhydrazone derivatives containing furan

European Journal of Medicinal Chemistry

Volumn 45, Issue 12, 2010, Pages 5576-5584

  Cui, Zining ^a   Li, Ying ^a   Ling, Yun ^a   Huang, Juan ^a   Cui, Jingrong ^b   Wang, Ruiqing ^b   Yang, Xinling ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Acylhydrazone; Antitumor activity; Configurational isomer; Synthesis; Toxicity

Indexed keywords

2 CHLOROBENZALDEHYDE 5 (4 FLUOROPHENYL) 2 FUROYL HYDRAZONE; 2 HYDROXYBENZALDEHYDE 5 (2,4 DIFLUOROPHENYL) 2 FUROYL HYDRAZONE; 2 HYDROXYBENZALDEHYDE 5 (4 FLUOROPHENYL) 2 FUROYL HYDRAZONE; 2 METHOXYBENZALDEHYDE 5 (2,4 DIFLUOROPHENYL) 2 FUROYL HYDRAZONE; 3 BROMOBENZALDEHYDE 5 (2 FLUOROPHENYL) 2 FUROYL HYDRAZONE; 3 METHYLBENZALDEHYDE 5 (2 NITROPHENYL) 2 FUROYL HYDRAZONE; 4 BROMOBENZALDEHYDE 5 (2 CHLOROPHENYL) 2 FUROYL HYDRAZONE; 4 CHLOROBENZALDEHYDE 5 (2 FLUOROPHENYL) 2 FUROYL HYDRAZONE; 4 HYDROXYBENZALDEHYDE 5 (4 FLUOROPHENYL) 2 FUROYL HYDRAZONE; 5 (2' CHLOROPHENYL)FURAN 2 CARBALDEHYDE 2 METHOXYBENZOYL HYDRAZONE; 5 (2' FLUOROPHENYL)FURAN 2 CARBALDEHYDE 2 CHLOROBENZOYL HYDRAZONE; 5 (2' NITROPHENYL)FURAN 2 CARBALDEHYDE 3 METHYLBENZOYL HYDRAZONE; 5 (2',4'' DIFLUOROPHENYL)FURAN 2 CARBALDEHYDE 2 METHOXYBENZOYL HYDRAZONE; 5 (2'4, DIFLUOROPHENYL)FURAN 2 CARBALDEHYDE 2 HYDROXYBENZOYL HYDRAZONE; 5 (3' FLUOROPHENYL)FURAN 2 CARBALDEHYDE 4 BROMOBENZOYL HYDRAZONE; 5 (4' CHLOROPHENYL)FURAN 2 CARBALDEHYDE 2 BENZOYL HYDRAZONE; 5 (4' FLUOROPHENYL)FURAN 2 CARBALDEHYDE 2 HYDROXYBENZOYL HYDRAZONE; ANTINEOPLASTIC AGENT; BENZALDEHYDE 5 (4 CHLOROPHENYL) 2 FUROYL HYDRAZONE; DOXORUBICIN; FURAN; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG DESIGN; DRUG DETERMINATION; DRUG POTENCY; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; HL-60 CELLS; HUMANS; HYDRAZONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78649319059     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.09.007     Document Type: Article

References (50)

1. A.V. Hoffbrand, K. Ganeshaguru, J.W.L. Hooton, and M.H.N. Tattersall Br. J. Haematol. 33 1976 517 526
2. R.J. Bergeron, P.F. Cavanaugh Jr., S.J. Kline, R.G. Hughes Jr., G.T. Elliott, and C.W. Porter Biochem. Biophys. Res. Commun. 121 1984 848 854
3. K.P. Hoyes, R.C. Hider, and J.B. Porter Cancer Res. 52 1992 4591 4599
4. P.A. Seligman, R.B. Schleicher, G. Siriwardana, J. Domenico, and E.W. Gelfand Blood 82 1993 1608 1617
5. S.V. Torti, F.M. Torti, S.P. Whitman, M.W. Brechbiel, G. Park, and R.P. Planalp Blood 92 1998 1384 1389
6. P.V. Bernhardt, P.C. Sharpe, M. Islam, D.B. Lovejoy, D.S. Kalinowski, and D.R. Richardson J. Med. Chem. 52 2009 407 415
7. D.R. Richardson, P.C. Sharpe, D.B. Lovejoy, D. Senaratne, D.S. Kalinowski, M. Islam, and P.V. Bernhardt J. Med. Chem. 49 2006 6510 6521
8. D.S. Kalinowski, Y. Yu, P.C. Sharpe, M. Islam, Y. Liao, D.B. Lovejoy, N. Kumar, P.V. Bernhardt, and D.R. Richardson J. Med. Chem. 50 2007 3716 3729
9. M. Whitnall, J. Howard, P. Ponka, and D.R. Richardson Proc. Natl. Acad. Sci. U.S.A. 103 2006 14901 14906
10. J. Blatt, and S. Stitely Cancer Res. 47 1987 1749 1750
11. Z. Estrov, A. Tawa, X.H. Wang, I.D. Dube, H. Sulh, A. Cohen, E.W. Gelfand, and M.H. Freedman Blood 69 1987 757 761
12. D.L. Becton, and P. Bryles Cancer Res. 48 1988 7189 7192
13. A. Donfrancesco, G. Deb, C. Dominici, D. Pileggi, M.A. Castello, and L. Helson Cancer Res. 50 1990 4929 4930
14. A. Donfrancesco, G. Deb, C. Dominici, A. Angioni, M. Caniglia, L. De Sio, P. Fidani, A. Amici, and L. Helson Am. J. Clin. Oncol 15 1992 319 322
15. A. Donfrancesco, B. De Bernardi, M. Carli, A. Mancini, M. Nigro, L. De Sio, F. Casale, S. Bagnulo, L. Helson, and G. Deb Eur. J. Cancer 31A 1995 612 615
16. D.R. Richardson Can. J. Physiol. Pharmacol 75 1997 1164 1180
17. K. Ogata, A. Watanabe, T. Yunokuchi, and A. Toyota Inorg. Chem. Commun. 11 2008 215 219
18. R. Gup, and B. Kirkan Spectrochim. Acta, Part A 64A 2006 809 815
19. A. Bacchi, I. Ivanovic-Burmazovic, G. Pelizzi, and K. Andjelkovic Inorg. Chim. Acta 313 2001 109 119
20. N.M.H. Salem Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 35 2005 369 377
21. P.V. Bernhardt, L.M. Caldwell, T.B. Chaston, P. Chin, and D.R. Richardson J. Biol. Inorg. Chem. 8 2003 866 880
22. D.R. Richardson, and P.V. Bernhardt J. Biol. Inorg. Chem. 4 1999 266 273
23. D.S. Kalinowski, P.C. Sharpe, P.V. Bernhardt, and D.R. Richardson J. Med. Chem. 50 2007 6212 6225
24. C.A.M. Fraga, and E.J. Barreiro Curr. Med. Chem. 13 2006 167 198
25. L.M. Lima, F.S. Frattani, J.L. dos Santos, H.C. Castro, C.A.M. Fraga, R.B. Zingali, and E.J. Barreiro Eur. J. Med. Chem. 43 2008 348 356
26. P. Diaz, S.S. Phatak, J. Xu, F. Astruc-Diaz, C.N. Cavasotto, and M. Naguib J. Med. Chem. 52 2009 433 444
27. Y.B. Dong, Y. Geng, J.P. Ma, and R.Q. Huang Inorg. Chem. 44 2005 1693 1703
28. J.R. Andreatta, G.B. Cieslinski, M. Batool, X.Z. Sun, M.W. George, E.N. Brothers, D.J. Darensbourg, and A.A. Bengali Inorg. Chem. 48 2009 7787 7793
29. S.M. Emam, F.A. El-Saied, S.A. Abou El-Enein, and H.A. El-Shater Spectrochim. Acta, Part A 72A 2009 291 297
30. S.S. Jr. Pelosi, US 3946049, 1976.
31. Chem. Abstr. 85 1976 21083
32. S.S. Jr. Pelosi, US 3962284, 1976.
33. Chem. Abstr. 85 1976 159860
34. H.A. Burch, R.E. White, G.C. Wright, and M.M. Goldenberg J. Pharm. Sci. 69 1980 107 114
35. X.L. Yang, D.Q. Wang, F.H. Chen, and Z.N. Zhang Pestic. Sci. 52 1998 282 286
36. Z.N. Cui, J. Huang, Y. Li, Y. Ling, X.L. Yang, and F.H. Chen Chin. J. Chem. 26 2008 916 922
37. Y. Li, B.J. Li, Y. Ling, H.J. Miao, Y.X. Shi, and X.L. Yang J. Agric. Food Chem. 58 2010 3037 3042
38. G.J. Karabatsos, J.D. Graham, and F.M. Vane J. Am. Chem. Soc. 84 1962 753 756
39. G.J. Karabatsos, and R.A. Taller J. Am. Chem. Soc. 85 1963 3624 3629
40. G.J. Karabatsos, and T.H. Althuis Tetrahedron Lett. 8 1967 4911 4914
41. Z.N. Cui, Z. Wang, Y. Li, X.Y. Zhou, Y. Ling, and X.L. Yang Chin. J. Org. Chem. 27 2007 1300 1304
42. A. Krutosikova, J. Kovac, and V. Sykora Collect. Czech. Chem. Commun. 39 1974 1892 1897
43. Bruker SMART 1998 Bruker AXS Inc. Madison, Wisconsin, USA
44. Bruker Smart-NT Version 5.05 1998 Bruker AXS Inc. Madsion, Wisconsin, USA
45. G.M. Sheldrick SHELXS97 and SHELXL97 1997 University of Göttingen Germany
46. Bruker Saint and SHELXTL 1999 Bruker AXS Inc. Madison, Wisconsin, USA
47. J. Berkson J. Am. Statistical Assoc. 39 1944 357 365
48. F. Denizot, and R. Lang J. Immunol. Methods 89 1986 271 277
49. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, and M. Boyd J. Natl. Cancer Inst 83 1991 757 766
50. Q. Liao, J.H. Yao, F. Li, S.G. Yuan, J.P. Doucet, A. Panaye, and B.T. Fan SAR QSAR Environ. Res. 15 2004 217 235