Synthesis and biological activities of 2-amino-1-arylidenamino imidazoles as orally active anticancer agents

Journal of Medicinal Chemistry

Volumn 53, Issue 6, 2010, Pages 2409-2417

  Li, Wen Tai ^a   Hwang, Der Ren ^a   Song, Jen Shin ^a   Chen, Ching Ping ^a   Chuu, Jiunn Jye ^a   Hu, Chih Bo ^a   Lin, Heng Liang ^a   Huang, Chen Lung ^a   Huang, Chiung Yi ^a   Tseng, Huan Yi ^a   Lin, Chu Chung ^a   Chen, Tung Wei ^a,b   Lin, Chi Hung ^b   Wang, Hsin Sheng ^a   Shen, Chien Chang ^a   Chang, Chung Ming ^a   Chao, Yu Sheng ^a   Chen, Chiung Tong ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^b NATIONAL YANG MING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 CHLOROBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (2,3 DICHLOROBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (2,3 DIHYDRONAPHTHALEN 4(1H) YLIDENEAMINO) 4 PHENYL 1H IMADAZOL 2 AMINE; 1 (3,4 DICHLOROBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (4 BROMOBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (4 CHLORO 2 NITROBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (2 METHOXYPHENYL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (5 CHLOROTHIOPHEN 2 YL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (PYRIDIN 2 YL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (PYRIDIN 3 YL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (THIAZOL 2 YL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (THIOPHEN 2 YL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 (THIOPHEN 3 YL) 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 BIPHENYL 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (4 CHLOROBENZYLIDENEAMINO) 4,5 DIPHENYL 1H IMIDAZOL 2 AMINE; 1 (4 FLUOROBENZYLIDENEAMINO) 4 (PYRIDIN 3 YL) 1H IMIDAZOL 2 AMINE; 1 (4 FLUOROBENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 (BENZYLIDENEAMINO) 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 [(3 METHYLTHIOPHEN 2 YL)METHYLENEAMINO] 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 [(QUINOLIN 4 YL)METHYLENEAMINO] 4 PHENYL 1H IMIDAZOL 2 AMINE; 1 [4 (TRIFLUOROMETHYL)BENZYLIDENEAMINO] 4 PHENYL 1H IMIDAZOL 2 AMINE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA; MICROTUBULE; MOUSE; NONHUMAN;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; LEUKEMIA P388; MICE; MICE, INBRED DBA; MICE, NUDE; MICROTUBULES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 77949859258     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901501s     Document Type: Article

References (34)

1. Uttamchandani, M.; Lu, H. S.; Yao, S. Q. Next generation chemical proteomic tools for rapid enzyme profiling. Acc Chem. Res. 2009, 2, 1183-1192.
2. Liu, B.; Li, S. J. Technological advances in high-throughput screening. Am. J. Pharmacogenomics 2004, 4, 263-276.
3. Hann, M. M.; Oprea, T. I. Pursuing the leadlikeness concept in pharmaceutical research. Curr. Opin. Chem. Biol. 2004, 8, 255-263.
4. Yang, X.; Chen, E.; Jiang, H.; Muszynski, K.; Harris, R. D.; Giardina, S. L.; Gromeier, M.; Mitra, G.; Soman, G. Evaluation of IRES-mediated, cell-type-specific cytotoxicity of poliovirus using a colorimetric cell proliferation assay. J. Virol. Methods 2009, 155, 44-54.
5. Cory, A. H.; Owen, T. C.; Barltrop, J. A.; Cory, J. G. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun. 1991, 5, 207-212.
6. Thabrew, M. I.; Hughes, R. D.; McFarlane, I. G. Screening of hepatoprotective plant components using a HepG2 cell cytotoxicity assay. J Pharm. Pharmacol. 1997, 49, 1132-1135.
7. Bleicher, K. H; Böhm, H.-J.; Müller, K.; Alanine, A. I. A guide to drug discovery: hit and lead generation: beyond high-throughput screening. Nat. Rev. Drug Discovery 2003, 2, 369-378.
8. Bennett, J. L. L.; Baker, H. T. Synthesis of potential anticancer agents. IV. 4-Nitro- and 4-amino-5-imidazole sulfones. J. Am. Chem. Soc. 1957, 79,2188-2191.
9. Lee, H. H.; Palmer, B. D.; Wilson, W. R.; Denny, W. A. Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard. Bioorg. Med. Chem. Lett. 1998, 8, 1741-1774.
10. Iradyan, M. A.; Iradyan, N. S.; Ovagimyan, A. A.; Stepanyan, G. M.; Arsenyan, F. G.; Garibdzhanyan, B. T. Imidazole derivatives XVIII. Synthesis and antitumor activity of some bis[2-chloroethyl]amino imidazole derivatives. Pharm. Chem. J. 1984, 18, 462-466.
11. Bielawski, K.; Bielawska, A.; Poplawska, B. Synthesis and cytotoxic activity of novel amidine analogues of bis(2-chloroethyl)amine. Arch. Pharm. Chem. Life Sci. 2009, 342, 484-490.
12. LaBarbera, D. V.; Modzelewska, K.; Glazar, A. I.; Gray, P. D.; Kaur, M.; Liu, T.; Grossman, D.; Harper, M. K.; Kuwada, S. K.; Moghal, N.; Ireland, C. M. The marine alkaloid naamidine A promotes caspase-dependent apoptosis in tumor cells. Anti-Cancer Drugs 2009, 20, 425-436.
13. Copp, B. R.; Fairchild, C. R.; Cornell, L.; Casazza, A. M.; Robinson, S.; Ireland, C. M. Naamidine A is an antagonist of the epidermal growth factor receptor and an in vivo active antitumor agent. J. Med. Chem. 1998, 41, 3909-3911.
14. Kanthou, C.; Tozer, G. M. Microtubule depolymerizing vascular disrupting agents: novel therapeutic agents for oncology and other pathologies. Int. J. Exp. Pathol. 2009, 90, 284-294.
15. De Rycker, M.; Rigoreau, L.; Dowding, S.; Parker, P. J. A highcontent, cell-based screen identifies micropolyin, a new inhibitor of microtubule dynamics. Chem. Biol. Drug Des. 2009, 73, 599-610.
16. Hait, W. N.; Hambley, T. W. Targeted cancer therapeutics. Cancer Res. 2009, 69, 1263-1267.
17. Budman, D. R. Vinorelbine (Navelbine): a third-generation vinca alkaloid. Cancer Invest. 1997, 15, 475-490.
18. Simoni, D.; Romagnoli, R.; Baruchello, R.; Rondanin, R.; Rizzi, M.; Pavani, M. G.; Alloatti, D.; Giannini, G.; Marcellini, M.; Riccioni, T.; Castorina, M.; Guglielmi, M. B.; Bucci, F.; Carminati, P.; Pisano, C. Novel combretastatin analogues endowed with antitumor activity. J. Med. Chem. 2006, 49, 3033-3044.
19. Zhou, J.; Giannakakou, P. Targeting microtubules for cancer chemotherapy. Curr. Med. Chem.: Anti-Cancer Agents 2005, 5, 10-12.
20. Carlson, R. O. New tubulin targeting agents currently in clinical development. Expert Opin. Invest. Drugs 2008, 17, 707-722.
21. Krimer, M. Z.; Makaev, F. Z.; Styngach, E. P.; Koretskii, A. G.; Pogrebnoi, S. I.; Kochug, A. I. Synthesis of substituted 2-amino- larylidenaminoimidazoles and 1-arylidenaminoimidazo[l,2-a]imidazoles. Chem. Heterocycl. Compd. 1996, 32, 1035-1039.
22. Kolos, N. N.; Orlov, V. D.; Paponov, B. V.; Shishkin, O. V. Synthesis of dihydro derivatives of 2-amino-4,5,7-triarylimidazo[l,5-b]pyridazine. Chem. Heterocycl. Compd. 1999, 35, 1207-1213.
23. Quattara, L.; Debaert, M.; Cavier, R. Synthese et activite antiparasitaire de nouveaux derives du nitro-5 imidazol. Farmaco 1987, 42, 449-456.
24. Ivashchenko, A. V.; Lazareva, V. T.; Prudnikova, E. K.; Ivashchenko, S. P.; Rumyantsev, V. G. Synthesis of 1, 2-diaminoimidazole guanylhydrazone with α-haloalkyl aryl ketones. Chem. Heterocycl. Compd. 1982, 18, 185-189.
25. 15N) NMR study. Monatsh. Chem. 2004, 135, 173-184.
26. Mahboobi, S.; Sellmer, A.; Höcher, H.; Eichhorn, E.; Bär, T.; Schmidt, M.; Maier, T.; Stadlwieser, J. F.; Beckers, T. L. [4-(Imidazol-l-yl) thiazol-2-yl]phenylamines. A novel class of highly potent colchicine site binding tubulin inhibitors: synthesis and cytotoxic activity on selected human cancer cell lines. J. Med. Chem. 2006, 49, 5169-15116
27. Liberatore, A. M.; Coulomb, H.; Pons, D.; Dutruel, O.; Kasprzyk, P. G.; Carlson, M.; Nelson, A. S.; Newman, S. P.; Stengel, C.; Auvray, P.; Hesry, V.; Foll, B.; Narboux, N.; Morlais, D.; Le Moing, M.; Bernetiere, S.; Dellile, R.; Camara, J.; Ferrandis, E.; Bigg, D. C.; Prévost, G. P. IRC-083927 is a new tubulin binder that inhibits growth of human tumor cells resistant to standard tubulin-binding agents. Mol. Cancer Ther. 2008, 7, 2426-2434.
28. Goodwin, C. J.; Holt, S. J.; Downes, S.; Marshall, N. J. Microculture tetrazolium assays: a comparison between two new tetrazolium salts, XTT and MTS. J. Immunol. Methods 1995, 179, 95-103.
29. Chuu, J.-J.; Liu, J. M.; Tsou, M. H.; Huang, C.-L.; Chen, C.-P.; Wang, H.-S.; Chen, C.-T. Effects of paclitaxel and doxorubicin in histocultures of hepatocelular carcinomas. J. Biomed. Sci. 2007, 14, 233-244.
30. Li, W. T.; Hwang, D. R.; Chen, C. P.; Shen, C. W.; Huang, C. L.; Chen, T. W.; Lin, C. H.; Chang, Y. L.; Chang, Y. Y.; Lo, Y. K.; Tseng, H. Y.; Lin, C. C.; Song, J. S.; Chen, H. C.; Chen, S. J.; Wu, S. H.; Chen, C. T. Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as p.o. active anticancer agents. J. Med. Chem. 2003, 46, 1706-1715.
31. Zuse, A.; Schmidt, P.; Baasner, S.; Böhm, K. J.; Müller, K.; Gerlach, M.; Günther, E. G.; Unger, E.; Prinz, H. Sulfonate derivatives of naphtho[2,3-è]thiophen-4(9//)-one and 9(X0H)-anthracenone as highly active antimicrotubule agents. Synthesis, antiproliferative activity, and inhibition of tubulin polymerization. J. Med. Chem. 2007, 50, 6059-6066.
32. Prinz, H.; Ishii, Y.; Hirano, T.; Stoiber, T.; Camacho Gomez, J. A.; Schmidt, P.; Düssmann, H.; Burger, A. M.; Prehn, J. H.; Günther, E. G..; Unger, E.; Umezawa, K. Novel benzylidene-9(10H)-anthracenones as highly active antimicrotubule agents. Synthesis, antiproliferative activity, and inhibition of tubulin polymerization. J. Med. Chem. 2003, 46, 3382-3394.
33. Kuo, C. C; Hsieh, H. P.; Pan, W. Y.; Chen, C. P.; Liou, J. P.; Lee, S, J.; Chang, Y. L.; Chen, L. T.; Chen, C. T.; Chang, J. Y. BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004, 64, 4621-4628
34. Singer, W. D.; Hersh, R. T.; Himes, R. H. Effect of solution variables on the binding of vinblastine to tubulin. Biochem. Pharmacol. 1988, 37, 2691-2696.