Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 7, 2011, Pages 2306-2325

  O'Boyle, Niamh M ^a   Greene, Lisa M ^a   Bergin, Orla ^b   Fichet, Jean Baptiste ^a   McCabe, Thomas ^a   Lloyd, David G ^a   Zisterer, Daniela M ^a   Meegan, Mary J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Lactam; Antiproliferative; Azetidinone; Colchicine; Combretastatin A 4 analogues; Cytotoxicity; Reformatsky reaction; Staudinger reaction; Structure activity; Tubulin

Indexed keywords

1 (3,4,5 TRIMETHOXYPHENYL) 3,4 DI(THIOPHEN 2 YL)AZETIDIN 2 ONE; 1 (3,4,5 TRIMETHOXYPHENYL) 4 (NAPHTHALEN 1 YL) 3 (THIOPHEN 2 YL)AZETIDIN 2 ONE; 1 (3,4,5 TRIMETHOXYPHENYL) 4 (NAPHTHALEN 2 YL) 3 (THIOPHEN 2 YL)AZETIDIN 2 ONE; 3 CYCLOHEXYL 4 (4 METHOXYPHENYL) 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 3 FURAN 3 YL 4 (4 METHOXYPHENYL) 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXY 3 NITROPHENYL) 3 THIOPEN 2 YL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 (1 METHYL 1H INDOL 2 YL) 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 (THIOPHEN 2 YLMETHYL) 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 METHYL 3 PHENYL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 NAPHTHALEN 1 YL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 NAPHTHALEN 2 YL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 THIOPHEN 2 YL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3 THIOPHEN 3 YL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 (4 METHOXYPHENYL) 3,3 DIPHENYL 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; 4 [3 [(TERT BUTYLDIMETHYLSILYL)OXY] 4 METHOXYPHENYL] 3 (THIOPHEN 2 YL) 1 (3,4,5 TRIMETHOXYPHENYL)AZETIDIN 2 ONE; ANTINEOPLASTIC AGENT; ASPARAGINASE; AZETIDIN 2 ONE DERIVATIVE; AZETIDINONE DERIVATIVE; COMBRETASTATIN A4; CYTOTOXIC AGENT; MAYTANSINE; MITHRAMYCIN; PACLITAXEL; RHIZOXIN; TIOGUANINE; TRIMETREXATE; TUBULIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINCRISTINE SULFATE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN; CELL STRAIN MCF 7; CELL STRAIN MDA MB 231; CELL STRAIN NCI60; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; IC 50; ISOMERIZATION; MOUSE; NONHUMAN;

ANIMALS; AZETIDINES; BETA-LACTAMS; BREAST NEOPLASMS; CELL GROWTH PROCESSES; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; EPITHELIAL CELLS; FEMALE; HUMANS; MICE; MODELS, MOLECULAR; PREGNANCY; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN;

MURINAE;

EID: 79953166386     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.02.022     Document Type: Article

References (69)

1. K.H. Downing Annu. Rev. Cell Dev. Biol. 16 2000 89
2. M. Kavallaris Nat. Rev. Cancer 10 2010 194
3. C. Dumontet, and M.A. Jordan Nat. Rev. Drug Discovery 9 2010 790
4. G.M. Cragg, D.G. Kingston, and D.J. Newman Anticancer Agents from Natural Products 2005 CRC press Florida
5. G.R. Pettit, S.B. Singh, E. Hamel, C.M. Lin, D.S. Alberts, and D. Garcia-Kendall Experientia 45 1989 209
6. J.M. Watt, and M. Gerdina The Medicinal and Poisonous Plants of Southern and Eastern Africa 1962 E&S Livingstone Ltd Edinburgh and London
7. E. Hamel, and C.M. Lin Biochem. Pharmacol. 32 1983 3864
8. G.M. Tozer, C. Kanthou, C.S. Parkins, and S.A. Hill Int. J. Exp. Pathol. 83 2002 21
9. G.R. Pettit, and J.W. Lippert Anticancer Drug Des. 15 2000 203
10. K. Strebhardt, and A. Ullrich Nat. Rev. Cancer 8 2008 473
11. G.R. Pettit, C. Temple Jr., V.L. Narayanan, R. Varma, M.J. Simpson, M.R. Boyd, G.A. Rener, and N. Bansal Anticancer Drug Des. 10 1995 299
12. N.H. Nam Curr. Med. Chem. 10 2003 1697
13. N.-H. Nam, Y. Kim, Y.-J. You, D.-H. Hong, H.-M. Kim, and B.-Z. Ahn Bioorg. Med. Chem. Lett. 12 2002 1955
14. I. Barrett, M. Carr, N. O'Boyle, L.M. Greene, A. Knox, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan J. Enzyme Inhib. Med. Chem. 25 2010 180
15. L. Lee, L.M. Robb, M. Lee, R. Davis, H. Mackay, S. Chavda, B. Babu, E.L. O'Brien, A.L. Risinger, S.L. Mooberry, and M. Lee J. Med. Chem. 53 2010 325
16. L. Wang, K.W. Woods, Q. Li, K.J. Barr, R.W. McCroskey, S.M. Hannick, L. Gherke, R.B. Credo, Y.H. Hui, K. Marsh, R. Warner, J.Y. Lee, N. Zielinski-Mozng, D. Frost, S.H. Rosenberg, and H.L. Sham J. Med. Chem. 45 2002 1697
17. N.-H. Nam, Y. Kim, Y.-J. You, D.-H. Hong, H.-M. Kim, and B.-Z. Ahn Bioorg. Med. Chem. Lett. 11 2001 3073
18. B.L. Flynn, G.P. Flynn, E. Hamel, and M.K. Jung Bioorg. Med. Chem. Lett. 11 2001 2341
19. G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, and A.A. Genazzani J. Med. Chem. 49 2006 3033
20. I. Banik, F.F. Becker, and B.K. Banik J. Med. Chem. 46 2003 12
21. S. Ruf, G. Neudert, S. Gürtler, R. Grünert, P.J. Bednarski, and H.-H. Otto Monatsh. Chem. 139 2008 847
22. L. Sun, N.I. Vasilevich, J.A. Fuselier, S.J. Hocart, and D.H. Coy Bioorg. Med. Chem. Lett. 14 2004 2041
23. M. Carr, L.M. Greene, A.J.S. Knox, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Eur. J. Med. Chem. 45 2010 5752
24. N.M. O'Boyle, M. Carr, L.M. Greene, O. Bergin, S.M. Nathwani, T. McCabe, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan J. Med. Chem. 53 2010 8569
25. L.M. Greene, S.M. Nathwani, S.A. Bright, D. Fayne, A. Croke, M. Gagliardi, A.M. McElligott, L. O'Connor, M. Carr, N.O. Keely, N.M. O'Boyle, P. Carroll, B. Sarkadi, E. Conneally, D.G. Lloyd, M. Lawler, M.J. Meegan, and D.M. Zisterer J. Pharmacol. Exp. Therap. 335 2010 302
26. B.K. Banik, I. Banik, and F.F. Becker Bioorg. Med. Chem. 13 2005 3611
27. R. Ocampo, and J.W.R. Dolbier Tetrahedron 60 2004 9325
28. H. Gross, and B. Costisella Angew. Chem., Int. Ed. Engl. 7 1968 391
29. C.R. Degenhardt Synth. Commun. 12 1982 415
30. M. Cushman, H.M. He, C.M. Lin, and E. Hamel J. Med. Chem. 36 1993 2817
31. P.G.M. Wuts, and T.W. Greene Greene's Protective Groups in Organic Synthesis 4th ed. 2007 John Wiley & Sons Hoboken, New Jersey
32. G.I. Georg The Organic Chemistry of β-Lactams 1992 VCH New York and Cambridge
33. A.K. Bose, G. Spiegelman, and M.S. Manhas Tetrahedron Lett. 12 1971 3167
34. D. Krishnaswamy, V.V. Govande, V.K. Gumaste, B.M. Bhawal, and A.R.A.S. Deshmukh Tetrahedron 58 2002 2215
35. L. Cotarca, P. Delogu, A. Nardelli, and V. Sunjic Synthesis 1996 553
36. S.B. Singh, and G.R. Pettit Synth. Commun. 17 1987 877
37. A.B.S. Maya, C. Perez-Melero, C. Mateo, D. Alonso, J.L. Fernandez, C. Gajate, F. Mollinedo, R. Pelaez, E. Caballero, and M. Medarde J. Med. Chem. 48 2005 556
38. R. Mayrhofer, and H.-H. Otto Synthesis 1980 247
39. E.J. Corey, and J.W. Suggs Tetrahedron Lett. 31 1975 2647
40. T. Mosmann J. Immunol. Methods 65 1983 55
41. National Cancer Institute (NCI)/Division of Cancer Treatment and Diagnosis (DCTD)/Developmental Therapeutics Program (DTP), 2008.
42. K.D. Paull, R.H. Shoemaker, L. Hodes, A. Monks, D.A. Scudiero, L. Rubinstein, J. Plowman, and M.R. Boyd J. Natl. Cancer. Inst. 81 1989 1088
43. DTP Human Tumour Cell Line Screen Standard Agent Database. http://dtp.nci.nih.gov/docs/cancer/searches/standard-agent.html (11 May).
44. K.D. Paull, C.M. Lin, L. Malspeis, and E. Hamel Cancer Res. 52 1992 3892
45. E.E. Furlong, N.K. Keon, F.D. Thornton, T. Rein, and F. Martin J. Biol. Chem. 271 1996 29688
46. J. Murtagh, E. McArdle, E. Gilligan, L. Thornton, F. Furlong, and F. Martin J. Cell Biol. 166 2004 133
47. D. Simoni, R. Romagnoli, R. Baruchello, R. Rondanin, M. Rizzi, M.G. Pavani, D. Alloatti, G. Giannini, M. Marcellini, T. Riccioni, M. Castorina, M.B. Guglielmi, F. Bucci, P. Carminati, and C. Pisano J. Med. Chem. 49 2006 3143
48. J.P. Liou, Y.L. Chang, F.M. Kuo, C.W. Chang, H.Y. Tseng, C.C. Wang, Y.N. Yang, J.Y. Chang, S.J. Lee, and H.P. Hsieh J. Med. Chem. 47 2004 4247
49. R. Gastpar, M. Goldbrunner, D. Marko, and E. von Angerer J. Med. Chem. 41 1998 4965
50. A. Dorleans, B. Gigant, R.B.G. Ravelli, P. Maillet, V. Mikol, and M. Knossow Proc. Natl. Acad. Sci. U.S.A. 106 2009 13775
51. R.B.G. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, and M. Knossow Nature 428 2004 198
52. J.M. Andreu, B. Perez-Ramirez, M.J. Gorbunoff, D. Ayala, and S.N. Timasheff Biochemistry 37 1998 8356
53. T.L. Nguyen, C. McGrath, A.R. Hermone, J.C. Burnett, D.W. Zaharevitz, B.W. Day, P. Wipf, E. Hamel, and R. Gussio J. Med. Chem. 48 2005 6107
54. F. Lara-Ochoa, and G. Espinosa-Pérez Tetrahedron Lett. 48 2007 7007
55. A.M. Clark, and P. Labute J. Chem. Inf. Model. 47 2007 1933
56. G.R. Pettit, S.B. Singh, and G.M. Cragg J. Org. Chem. 66 1985 406
57. S. Darvesh, R.S. McDonald, K.V. Darvesh, D. Mataija, S. Conrad, G. Gomez, R. Walsh, and E. Martin Bioorg. Med. Chem. 15 2007 6367
58. Y. Poirier, L. Legrand, and N. Lozac'h Bull. Soc. Chim. Fr. 1966 1054
59. M. D'hooghe, S. Dekeukeleire, K. Mollet, C. Lategan, P.J. Smith, K. Chibale, and N. De Kimpe J. Med. Chem. 52 2009 4058
60. Y. Yang, G. Carta, M.B. Peters, T. Price, N. O'Boyle, A.J.S. Knox, D. Fayne, D.C. Williams, M.J. Meegan, and D.G. Lloyd Mol. Inf. 29 2010 421
61. Cytoskeleton, Tubulin Polymerization Assay Kit Manual (Cat. # CDS03 and BK006); 2009, pp. 1-18.
62. T. Schulz-Gasch, and M. Stahl J. Mol. Model. 9 2003 47
63. M. Feher, and C.I. Williams J. Chem. Inf. Model. 2009
64. T. Takagi, M. Amano, and M.J. Tomimoto Chem. Inf. Model. 49 2009 1377
65. MOEv2009.10, developed and distributed by Chemical Computing Group. http://www.chemcomp.com.
66. Software Reference Manual, shelxtl, An Integrated System for Data Collection, Processing, Structure Solution and Refinement; Bruker Analytical X-ray Systems: Madison, WI, 2001.
67. G. La Regina, T. Sarkar, R. Bai, M.C. Edler, R. Saletti, A. Coluccia, F. Piscitelli, L. Minelli, V. Gatti, C. Mazzoccoli, V. Palermo, C. Mazzoni, C. Falcone, A.I. Scovassi, V. Giansanti, P. Campiglia, A. Porta, B. Maresca, E. Hamel, A. Brancale, E. Novellino, and R. Silvestri J. Med. Chem. 52 2009 7512
68. S. Messaoudi, B. Treguier, A. Hamze, O. Provot, J.-F. Peyrat, J.R. De Losada, J.-M. Liu, J. Bignon, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami J. Med. Chem. 52 2009 4538
69. C. Mousset, A. Giraud, O. Provot, A. Hamze, J. Bignon, J.-M. Liu, S. Thoret, J. Dubois, J.-D. Brion, and M. Alami Bioorg. Med. Chem. Lett. 18 2008 3266