Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 14, 2012, Pages 4279-4289

  Hayashi, Yoshio ^a,b   Yamazaki, Yuri ^a,b   Sumikura, Makiko ^b   Masuda, Yurika ^a   Hayashi, Yoshiki ^a   Yasui, Hiroyuki ^b   Kiso, Yoshiaki ^b   Chinen, Takumi ^c   Usui, Takeo ^c   Yakushiji, Fumika ^a   Potts, Barbara ^d   Neuteboom, Saskia ^d   Palladino, Michael ^d   Lloyd, George Kenneth ^d  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^c UNIVERSITY OF TSUKUBA   (Japan)

^d Nereus Pharmaceuticals Inc   (United States)

Author keywords

Anticancer drug; Benzophenone; Diketopiperazine; Microtubule depolymerizing activity; Vascular disrupting agent

Indexed keywords

2 CHLORO N METHOXY N METHYLBENZAMIDE; 3 (2 METHOXYBENZOYL)BENZONITRILE; 3 (2,3 DIMETHOXYBENZOYL)BENZONITRILE; 3 (2,4 DIMETHOXYBENZOYL)BENZONITRILE; 3 (3 METHOXYBENZOYL)BENZONITRILE; 3 (3,4 DIMETHOXYBENZOYL)BENZONITRILE; 3 (4 BENZOYLBENZYLIDENE) 6 [(5 TERT BUTYL 1H IMIDAZOL 4 YL)METHYLENE]PIPERAZINE 2,5 DIONE; 3 (4 METHOXYBENZOYL)BENZONITRILE; 3 [(5 TERT BUTYL 1H IMIDAZOL 4 YL)METHYLENE] 6 [(9 OXO FLUOREN 2 YL)METHYLENE]PIPERAZINE 2,5 DIONE; 3 [(5 TERT BUTYL 1H IMIDAZOL 4 YL)METHYLENE] 6 [3 (4 FLUOROBENZOYL)BENZYLIDENE]PIPERAZINE 2,5 DIONE; 3 [(5 TERT BUTYL 1H IMIDAZOL 4 YL)METHYLENE] 6 [3 [HYDROXY(PHENYL)METHYL]BENZYLIDENE]PIPERAZINE 2,5 DIONE; 3 CHLORO N METHOXY N METHYLBENZAMIDE; 4 BROMO N METHOXY N METHYLBENZAMIDE; 4 CHLORO N METHOXY N METHYLBENZAMIDE; 4 FLUORO N METHOXY N METHYLBENZAMIDE; BENZOPHENONE DERIVATIVE; CA 4; COLCHICINE; KPU 105; KPU 2; N METHOXY N METHYL 4 (TRIFLUOROMETHYL)BENZAMIDE; N,2 DIMETHOXY N METHYLBENZAMIDE; N,2,3 TRIMETHOXY N METHYLBENZAMIDE; N,2,4 TRIMETHOXY N METHYLBENZAMIDE; N,3 DIMETHOXY N METHYLBENZAMIDE; N,3,4 TRIMETHOXY N METHYLBENZAMIDE; N,3,4,5 TETRAMETHOXY N METHYLBENZAMIDE; N,4 DIMETHOXY N METHYLBENZAMIDE; PIPERAZINE DERIVATIVE; PLINABULIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; CYTOTOXICITY; DEPOLYMERIZATION; DISSOCIATION CONSTANT; DRUG ACTIVITY; DRUG CONFORMATION; DRUG EFFICACY; DRUG POTENCY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; MICROTUBULE; MITOSIS SPINDLE; PROCESS OPTIMIZATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BENZOPHENONES; CELL PROLIFERATION; COLCHICINE; CRYSTALLOGRAPHY, X-RAY; DIKETOPIPERAZINES; HELA CELLS; HT29 CELLS; HUMANS; MICROTUBULES; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN MODULATORS;

EID: 84863217186     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.05.059     Document Type: Article

References (47)

1. E. Nogales Annu. Rev. Biochem. 69 2000 277
2. J. Zhou, and P. Giannakakou Curr. Med. Chem. Anti-Cancer Agents 5 2005 65
3. C. Dumontet, and M.A. Jordan Nat. Rev. Drug Disc. 9 2010 790
4. M. Suffness, and M.E. Wall M. Suffness, Taxol: Science and Applications 1995 CRC Press Boca Raton, FL 3
5. T.M. Mekhail, and M. Markman Expert Opin. Pharmacother. 3 2002 755
6. E.K. Rowinsky, and R.C. Donehower Pharmacol. Ther. 52 1991 35
7. R.J. Ludford J. Natl. Cancer Inst. 6 1945 89
8. S.C. Remick Horizons in Cancer Therapeutics: From Bench to Bedside 3 2002 16
9. M.J. Pilat, and M.J. LoRusso J. Cell. Biochem. 99 2006 1021
10. C.M. Lin, H.H. Ho, G.R. Pettit, and E. Hamel Biochemistry 28 1989 6984
11. G.R. Pettit, S.B. Singh, M.R. Boyd, E. Hamel, R.K. Pettit, J.M. Schmidt, and F. Hogan J. Med. Chem. 38 1995 1666
12. P.D. Davis, G.J. Dougherty, D.C. Blakey, S.M. Galbraith, G.M. Tozer, A.L. Holder, M.A. Naylor, J. Nolan, M.R.L. Stratford, D.J. Chaplin, and S.A. Hill Cancer Res. 62 2002 7247
13. G. Micheletti, M. Poli, P. Borsotti, M. Martinelli, B. Imberti, G. Taraboletti, and R. Giavazzi Cancer Res. 63 2003 1534
14. K. Ohsumi, T. Hatanaka, R. Nakagawa, Y. Fukuda, Y. Morinaga, Y. Suga, Y. Nihei, K. Ohishi, Y. Akiyama, and T. Tsuji Anti-Cancer Drug Des. 14 1999 539
15. K. Hori, and S. Saito Br. J. Cancer 89 2003 1334
16. N. Koyanagi, T. Nagasu, F. Fujita, T. Watanabe, K. Tsukahara, Y. Funahashi, M. Fujita, T. Taguchi, H. Yoshino, and K. Kitoh Cancer Res. 54 1994 1702
17. J.A. Segreti, J.S. Polakowski, K.A. Koch, K.C. Marsh, J.L. Bauch, S.H. Rosenberg, H.L. Sham, B.F. Cox, and G.A. Reinhart Cancer Chemother Pharmacol 54 2004 273
18. L.G.M. Daenen, J.M.L. Roodhart, Y. Shaked, and E.E. Voest Curr. Clin. Pharmacol. 5 2010 178
19. K. Kanoh, S. Kohno, T. Asari, T. Harada, J. Katada, M. Muramatsu, H. Kawashima, H. Sekiya, and I. Uno Bioorg. Med. Chem. Lett. 7 1997 2847
20. K. Kanoh, S. Kohno, J. Katada, J. Takahashi, and I. Uno J. Antibiot. 52 1999 134
21. K. Kanoh, S. Kohno, J. Katada, Y. Hayashi, M. Muramatsu, and I. Uno Biosci. Biotechnol., Biochem. 63 1999 1130
22. K. Kanoh, S. Kohno, J. Katada, J. Takahashi, I. Uno, and Y. Hayashi Bioorg. Med. Chem. 7 1999 1451
23. Y. Hayashi, S. Orikasa, K. Tanaka, K. Kanoh, and Y. Kiso J. Org. Chem 65 2000 8402
24. B. Nicholson, G.K. Lloyd, B.R. Miller, M.A. Palladino, Y. Kiso, Y. Hayashi, and S.T.C. Neulteboom Anti-Cancer Drugs 17 2006 25
25. Y. Yamazaki, K. Tanaka, B. Nicholson, G. Deyanat-Yazdi, B. Potts, T. Yoshida, A. Oda, T. Kitagawa, S. Orikasa, Y. Kiso, H. Yasui, M. Akamatsu, T. Chinen, T. Usui, Y. Shinozaki, F. Yakushiji, B.R. Miller, S. Neuteboom, M. Palladino, K. Kanoh, G.K. Lloyd, and Y. Hayashi J. Med. Chem. 55 2012 1056
26. G.R. Pettit, M.P. Grealish, D.L. Herald, M.R. Boyd, E. Hamel, and R.K. Pettit J. Med. Chem. 43 2000 2731
27. G.R. Pettit, B. Toki, D.L. Herald, P. Verdier-Pinard, M.R. Boyd, E. Hamel, and R.K. Pettit J. Med. Chem. 41 1998 1688
28. A. Ghinet, B. Rigo, J.-P. Hénichart, D.L. Broc-Ryckewaert, J. Pommery, N. Pommery, X. Thuru, B. Quesnel, and P. Gautret Bioorg. Med. Chem. 19 2011 6042
29. J.-P. Liou, J.-Y. Chang, C.-W. Chang, C.-Y. Chang, N. Mahindroo, F.-M. Kuo, and H.-P. Hsieh J. Med. Chem. 47 2004 2897
30. H.-P. Hsieh, J.-P. Liou, Y.-T. Lin, N. Mahindroo, J.-Y. Chang, Y.-N. Yang, S.-S. Chern, U.-K. Tan, C.-W. Chang, T.-W. Chen, C.-H. Lin, Y.-Y. Chang, and C.-C. Wang Bioorg. Med. Chem. Lett. 13 2003 101
31. H. Wehbe, C.M. Kearney, and K.G. Pinney Anticancer Res. 25 2005 3865
32. R. Schobert, B. Biersack, A. Dietrich, K. Effenberger, S. Knauer, and T. Mueller J. Med. Chem. 53 2010 6595
33. J.M. Andreu, B. Perez-Ramirez, M.J. Gorbunoff, D. Ayala, and S.N. Timasheff Biochemistry 37 1998 8356
34. N.-H. Nam, Y. Kim, Y.-J. You, D.-H. Hong, H.-M. Kim, and B.-Z. Ahn Bioorg. Med. Chem. Lett. 2002 1955 12
35. A. Zuse, P. Schmidt, S. Baasner, K.J. Böhm, K. Müller, M. Gerlach, E.G. Günther, E. Unger, and H. Prinz J. Med. Chem. 50 2007 6059
36. C. Álvarez, R. Álvarez, P. Corchete, C. Pérez-Melero, R. Peláez, and M. Medarde Bioorg. Med. Chem. 16 2008 8999
37. G.R. Pettit, M.D. Minardi, H.J. Rosenberg, E. Hamel, M.C. Bibby, S.W. Martin, M.K. Jung, R.K. Pettit, T.J. Cuthbertson, and J.-C. Chapuis J. Nat. Prod. 68 2005 1450
38. T.M. Beale, R.M. Myers, J.W. Shearman, D.S. Charnock-Jones, J.D. Brenton, F.V. Gergely, and S.V. Ley Med. Chem. Commun. 1 2010 202
39. E.R. Ottosen, M.D. Sorensen, F. Bjoerkling, T. Skak-Nielsen, M.S. Fjording, H. Aaes, and L. Binderup J. Med. Chem. 46 2003 5651
40. Y. Yamazaki, K. Kohno, H. Yasui, Y. Kiso, M. Akamatsu, B. Nicholson, G. Deyanat-Yazdi, S. Neuteboom, B. Potts, G.K. Lloyd, and Y. Hayashi ChemBioChem 9 2008 3074
41. E.J. Corey, and G. Schmidt Tetrahedron Lett. 5 1979 339
42. W.A. Loughlin, R.L. Marshall, A. Carreiro, and K.E. Elson Bioorg. Med. Chem. Lett. 10 2000 91
43. A. Folkes, M.B. Roe, S. Sohal, J. Golec, R. Faint, T. Brooks, and P. Charlton Bioorg. Med. Chem. Lett. 11 2001 2589
44. T. Watanabe, and T. Ishikawa Tetrahedron Lett. 40 1999 7795
45. Y. Yamazaki, M. Sumikura, K. Hidaka, H. Yasui, Y. Kiso, F. Yakushiji, and Y. Hayashi Bioorg. Med. Chem. 18 2010 3169
46. Y. Yamazaki, Y. Kido, K. Hidaka, H. Yasui, Y. Kiso, F. Yakushiji, and Y. Hayashi Bioorg. Med. Chem. 19 2011 595
47. M. Castoldi, and A.V. Popov Protein Expr. Purif. 32 2003 83