Convergent synthesis and biological evaluation of 2-amino-4-(3′, 4′,5′-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents

Journal of Medicinal Chemistry

Volumn 54, Issue 14, 2011, Pages 5144-5153

  Romagnoli, Romeo ^a   Baraldi, Pier Giovanni ^a   Brancale, Andrea ^b   Ricci, Antonio ^b   Hamel, Ernest ^c   Bortolozzi, Roberta ^d   Basso, Giuseppe ^d   Viola, Giampietro ^d  

^a UNIVERSITY OF FERRARA   (Italy)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c NATIONAL CANCER INSTITUTE   (United States)

^d UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 (3',4',5' TRIMETHOXYPHENYL) 5 ARYL THIAZOLE DERIVATIVE; COLCHICINE; COMBRETASTATIN A4; PHENYL GROUP; THIAZOLE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL DEATH; CELL KILLING; DRUG MECHANISM; HUMAN; HUMAN CELL; IC 50; MITOSIS; MULTIDRUG RESISTANCE; SYNTHESIS;

APOPTOSIS; CASPASES; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; COLCHICINE; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME ACTIVATION; HUMANS; MICROTUBULES; MITOSIS; MODELS, MOLECULAR; P-GLYCOPROTEIN; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; TUBULIN MODULATORS;

EID: 79960639980     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200392p     Document Type: Article

References (59)

1. Amos, L. A. Microtubule structure and its stabilisation Org. Biomol. Chem. 2004, 2, 2153-2160
2. Downing, K. H.; Nogales, E. Tubulin structure: insights into microtubule properties and functions Curr. Opin. Struct. Biol. 1998, 8, 785-791 (Pubitemid 29004677)
3. Honore, S.; Pasquier, E.; Braguer, D. Understanding microtubule dynamics for improved cancer therapy Cell. Mol. Life Sci. 2005, 62, 3039-3056 (Pubitemid 43004753)
4. Bhattacharyya, B.; Panda, D.; Gupta, S.; Banerjee, M. Antimitotic activity of colchicine and the structural basis for its interaction with tubulin Med. Res. Rev. 2008, 28, 155-183 (Pubitemid 350274963)
5. Hearn, B. R.; Shaw, S. J.; Myles, D. C. Microtubule targeting agents Compr. Med. Chem. II 2007, 7, 81-110
6. Mahindroo, N; Liou, J. P.; Chang, J. Y.; Hsieh, H. P. Antitubulin agents for the treatment of cancer. A medicinal chemistry update Expert Opin. Ther. Pat. 2006, 16, 647-691
7. Jordan, M. A.; Kamath, K. How do microtubule-targeted drugs works? An overview Curr. Cancer Drug Targets 2007, 7, 730-742
8. Risinger, A. L.; Giles, F. J.; Mooberry, S. L. Microtubule dynamics as a target in oncology Cancer Treat. Rev. 2008, 35, 255-261
9. Carson, R. O. New tubulin targeting agents currently in clinical development Expert Opin. Invest. Drugs 2008, 17, 707-722
10. Pettit, G. R.; Singh, S. B.; Hamel, E.; Lin, C. M.; Alberts, D. S.; Garcia-Kendall, D. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4 Experentia 1989, 45, 209-211 (Pubitemid 19062390)
11. Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin Biochemistry 1989, 28, 6984-6991 (Pubitemid 19219888)
12. McGown, A. T.; Fox, B. W. Differential cytotoxicity of combretastatins A1 and A4 in two daunorubucin-resistant P388 cell lines Cancer Chemother. Pharmacol. 1990, 26, 79-81 (Pubitemid 20122896)
13. Lippert, J. W., III. Vascular Disrupting Agents Bioorg. Med. Chem. 2007, 15, 605-615 (Pubitemid 44880701)
14. Cooney, M. M.; Ortiz, J.; Bukowski, R. M.; Remick, S. C. Novel vascular targeting disrupting agents: combretastatin A4 phosphate and related compounds Curr. Oncol. Rep. 2005, 7, 90-95 (Pubitemid 40485463)
15. Vincent, L.; Kermani, P.; Young, L. M.; Cheng, J.; Zhang, F.; Shido, K.; Lam, G.; Bompais-Vincent, H.; Zhu, Z.; Hicklin, D. J.; Bohlen, P.; Chaplin, D. J.; May, C.; Rafii, S. Combretastatin A4 phosphate induces rapid regression of tumor neovessels and growth through interference with vascular endothelial-cadherin signaling J. Clin. Invest. 2005, 115, 2992-3006 (Pubitemid 41567565)
16. Chaplin, D. J.; Hill, S. A. The development of combretastatin A4 phosphate as a vascular targeting agent Int. J. Radiat. Oncol. Biol. Phys. 2002, 54, 1491-1496 (Pubitemid 35380054)
17. Young, S. L.; Chaplin, D. J. Combretastatin A-4 phosphate: background and current clinical status Expert Opin. Invest. Drugs 2004, 13, 1171-1182 (Pubitemid 39242740)
18. Bilenker, J. H.; Flaherty, K. T.; Rosen, M.; Davis, L.; Gallagher, M.; Stevenson, J. P.; Sun, W.; Vaughn, D.; Giantonio, B.; Zimmer, R.; Scnall, M.; O'Dwyer, P. J. Phase I trial of combretastatin A-4 phospate with carboplatin Clin. Cancer Res. 2005, 11, 1527-1533 (Pubitemid 40315236)
19. Nam, N. H. Combretastatin A-4 analogues as antimitotic antitumor agents Curr. Med. Chem. 2003, 10, 1697-1722
20. Chaudari, A.; Pandeya, S. N.; Kumar, P.; Sharma, P. P.; Gupta, S.; Soni, N.; Verma, K. K.; Bhardwaj, G. Combretastain A-4 analogues as anticancer agents Mini Rev. Med. Chem. 2007, 12, 1186-1205 (Pubitemid 350303084)
21. Tron, G. C.; Pirali, T.; Sorba, G.; Pagliai, F.; Busacca, S.; Genazzani, A. A. Medicinal chemistry of combretastatin A4: present and future directions J. Med. Chem. 2006, 49, 3033-3044 (Pubitemid 43830499)
22. Hatanaka, T.; Fujita, K.; Ohsumi, K.; Nakagawa, R.; Fukuda, Y.; Nihei, Y.; Suga, Y.; Akiyama, Y.; Tsuji, T. Novel B-ring modified combretastatin analogues: synthesis and antineoplastic activity Bioorg. Med. Chem. Lett. 1998, 8, 3371-3374 (Pubitemid 28547074)
23. Gaukroger, K.; Hadfield, J. A.; Lawrence, N. J.; Nlan, S.; McGown, A. T. Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? Org. Biomol. Chem. 2003, 1, 3033-3037
24. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hui, Y.-H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmaokinetics, and in vivo antitumor activity evaluation J. Med. Chem. 2002, 45, 1697-1711 (Pubitemid 34293536)
25. Schobert, R.; Biersack, B.; Dietrich, A.; Effenberger, K.; Knauer, S.; Mueller, T. 4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and N -methylimidazoles that are cytotoxic against combretastatin A resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model J. Med. Chem. 2010, 53, 6595-66002
26. Bonezzi, K.; Taraboletti, G.; Borsotti, P.; Bellina, F.; Rossi, R.; Giavazzi, R. Vascular disrupting activity of tubulin-binding 1,5-diaryl-1 H -imidazoles J. Med. Chem. 2009, 52, 7906-7910
27. Ohsumi, K.; Hatanaka, T.; Fujita, K.; Nakagawa, R.; Fukuda, Y.; Nihai, Y.; Suga, Y.; Morinaga, Y.; Akiyama, Y.; Tsuji, T. Synthesis and antitumor activity of cis-restricted combretastatins 5-membered heterocyclic analogues Bioorg. Med. Chem. Lett. 1988, 8, 3153-3158
28. Tron, G. C.; Pagliai, F.; Sel Grosso, E.; Genazzani, A. A.; Sorba, G. Synthesis and cytotoxic evaluation of combretafurazans J. Med. Chem. 2005, 48, 3260-3258
29. Liu, T.; Dong, X.; Xue, N.; Wu, R.; He, Q.; Yang, B.; Hu, Y. Synthesis and biological evaluation of 3,4-biaryl-5-aminoisoxazole derivatives Bioorg. Med. Chem. 2009, 17, 6279-6285
30. Wu, M.; Li, W.; Yang, C.; Chen, D.; Ding, J.; Chen, Y.; Lin, L.; Xie, Y. Synthesis and activity of combretastatin A-4 analogues: 1,2,3-thiadiazoles as potent antitumor agents Bioorg. Med. Chem. Lett. 2007, 17, 869-873 (Pubitemid 46177634)
31. Odlo, K.; Hentzen, J.; Fournier dit Chabert, J.; Ducki, S.; Gani, A. B. S. M. O.; Sylte, I.; Skrede, M.; Florenes, V. A.; Hansen, T. V. 1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin Bioorg. Med. Chem. 2008, 16, 4829-4838 (Pubitemid 351625899)
32. Zhang, Q.; Peng, Y.; Wang, X. I.; Keeman, S. M.; Aurora., S.; Welsh, W. J. Highly potent triazole-based tubulin polymerization inhibitors J. Med. Chem. 2007, 50, 749-754 (Pubitemid 46332987)
33. Romagnoli, R.; Baraldi, P. G.; Cruz-Lopez, O.; Lopez-Cara, C.; Carrion, M. D.; Brancale, A.; Hamel, E.; Chen, L.; Bortolozzi, R.; Basso, G.; Viola, G. Synthesis and antitumor activity of 1,5-disubstituted 1,2,4-triazoles as cis-restricted combretastatin analogs J. Med. Chem. 2010, 53, 4248-4258
34. For a general review on palladium cross-coupling reactions see: Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 1995, 95, 2457-2483
35. Hamel, E. Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin Cell Biochem. Biophys. 2003, 38, 1-21 (Pubitemid 41270819)
36. Verdier-Pinard, P.; Lai, J.-Y.; Yoo, H.-D.; Yu, J.; Marquez, B.; Nagle, D. G.; Nambu, M.; White, J. D.; Falck, J. R.; Gerwick, W. H.; Day, B. W.; Hamel, E. Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells Mol. Pharmacol. 1998, 53, 62-67
37. Ravelli, R. B. G.; Gigant, B.; Curmi, P. A.; Jourdain, I.; Lachkar, S.; Sobel, A.; Knossow, M. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain Nature 2004, 428, 198-202 (Pubitemid 38374318)
38. Baguley, B. C. Multidrug resistance mechanism in cancer Mol. Biotechnol. 2010, 46, 308-316
39. Dupuis, M.; Flego, M.; Molinari, A.; Cianfriglia, M. Saquinavir induces stable and functional expression of the multidrug transporter P-glycoprotein in human CD4 T-lymphoblastoid CEM rev cells HIV Med. 2003, 4, 338-345 (Pubitemid 37304375)
40. Toffoli, G.; Viel, A.; Tuimoto, I.; Bisconti, G.; Rossi, G.; Baoiocchi, M. Pleiotropic-resistant phenotype is a multifactorial phenomenon in human colon carcinoma cell lines Br. J. Cancer 1991, 63, 51-56
41. Martello, L. A.; Verdier-Pinard, P.; Shen, H. J.; He, L.; Torres, K.; Orr, G. A.; Horwitz, S. B. Elevated level of microtubule destabilizing factors in a taxol-resistant/ dependent A549 cell line with an alpha-tubulin mutation Cancer Res. 2003, 63, 448-454
42. Chen, J. G.; Horwitz, S. B. Differential mitotic responses to microtubule-stabilizing and -destabilizing drugs Cancer Res. 2002, 62, 1935-1938 (Pubitemid 34408432)
43. Gascoigne, K. E.; Taylor, S. S. Cancer cells display profound intra and interline variation following prolonged exposure to antimitotic drugs Cancer Cell 2008, 14, 111-122
44. Mollinedo, F.; Gajate, C. Microtubules, microtubule-interfering agents and apoptosis Apoptosis 2003, 8, 413-450 (Pubitemid 37247987)
45. Clarke, P. R.; Allan, L. A. Cell-cycle control in the face of damage-a matter of life or death Trends Cell Biol. 2009, 19, 89-98
46. Vermes, I.; Haanen, C.; Steffens-Nakken, H.; Reutelingsperger, C. A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V J. Immunol. Methods 1995, 184, 39-51
47. Martin, S. J.; Reutelingsperger, C. P.; McGahon, A. J.; Rader, J. A.; van Schie, R. C.; Laface, D. M.; Green, D. R. Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl J. Exp. Med. 1995, 182, 1545-1556
48. Rothe, G.; Valet, G. Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,7′- dichlorofluorescein J. Leukocyte Biol. 1990, 47, 440-448 (Pubitemid 20155877)
49. Cai, J.; Jones, D. P. Superoxide in apoptosis. Mitochondrial generation triggered by cytochrome c loss J. Biol. Chem. 1998, 273, 11401-11404 (Pubitemid 28272028)
50. Nohl, H.; Gille, L.; Staniek, K. Intracellular generation of reactive oxygen species by mitochondria Biochem. Pharmacol. 2005, 69, 719-723 (Pubitemid 40248614)
51. Vakifahmetoglu-Norberg, H.; Zhivotovsky, B. The unpredictable caspase-2: what can it do? Trends Cell Biol 2010, 20, 150-159
52. Mhaidat, N. M.; Wang, Y.; Kiejda, K. A.; Zang, X. D.; Hersey, P. Docetaxel-induced apoptosis in melanoma cells is dependent on activation of caspase-2 Mol. Cancer Ther. 2007, 6, 752-761 (Pubitemid 46332476)
53. Ho, L. H.; Read, S. H.; Dorstyn, L.; Lambrusco, L.; Kumar, S. Caspase-2 is required for cell death induced by cytosketal disruption Oncogene 2008, 27, 3393-3404 (Pubitemid 351769315)
54. Vitale, I.; Antoccia, A.; Cenciarelli, C.; Crateri, P.; Meschini, S.; Arancia, G.; Pisano, C.; Tanzarella, C. Combretastatin A-4 and combretastatin derivative induce mitotic catastrophe dependent on spindle checkpoint and caspase-3 activation in non-small cell lung cancer cells Apoptosis 2007, 12, 155-166 (Pubitemid 46009511)
55. Cenciarelli, C.; Tanzarella, C.; Vitale, I.; Pisano, C.; Crateri, P.; Meschini., S.; Arancia, G.; Antoccia, A. The tubulin-depolymerising agent combretastatin-4 induces ectopic aster assembly and mitotic catastrophe in lung cancer cells H460 Apoptosis 2008, 13, 659-669
56. Castedo, M.; Perfettini, J. L.; Roumier, T.; Andreau, K.; Medema, R.; Kroemer, G. Cell death by mitotic catastrophe: a molecular definition Oncogene 2004, 23, 2825-2837 (Pubitemid 38638845)
57. Vakifahmetoglu, H.; Olsson, M.; Zhivotovsky, B. Death trough a tragedy: mitotic catastrophe Cell Death Differ. 2008, 15, 1153-1162 (Pubitemid 351850968)
58. Portugal, J.; Mansilla, S.; Bataller, M. Mechanisms of drug-induced mitotic catastrophe in cancer cells Curr. Pharm Des. 2010, 16, 69-78
59. 1) deficiency causes deformed nuclear architecture, centriole overduplication, polyploidy, and relaxed microtubule damage checkpoints in human hematopoietic cells Blood 1999, 15, 1390-1398 (Pubitemid 29076155)