Furanylazaindoles: Potent anticancer agents in vitro and in vivo

Journal of Medicinal Chemistry

Volumn 56, Issue 20, 2013, Pages 8008-8018

  Lee, Hsueh Yun ^a   Pan, Shiow Lin ^a   Su, Min Chieh ^a   Liu, Yi Min ^a   Kuo, Ching Chuan ^b   Chang, Yi Ting ^a   Wu, Jian Sung ^b   Nien, Chih Ying ^a   Mehndiratta, Samir ^a   Chang, Chi Yen ^b   Wu, Su Ying ^b   Lai, Mei Jung ^a   Chang, Jang Yang ^b,c   Liou, Jing Ping ^a  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^c NATIONAL CHENG KUNG UNIVERSITY HOSPITAL   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

7 (2 FURANYL) 1 (4 METHOXYBENZENESULFONYL) 6 AZAINDOLE; 7 (4 HYDROXYANILINO) 1 (4 METHOXYBENZENESULFONYL) 6 AZAINDOLE; 7 (4 METHOXYANILINO) 1 (4 METHOXYBENZENESULFONYL) 6 AZAINDOLE; 7 ANILINO 1 (4 METHOXYBENZENESULFONYL) 6 AZAINDOLE; 7 ANILINO 6 AZAINDOLE 1 BENZNESULFONAMIDE DERIVATIVE; ANTINEOPLASTIC AGENT; COLCHICINE; TUBULIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING SITE; BODY WEIGHT; CONTROLLED STUDY; CYTOTOXICITY; G2 PHASE CELL CYCLE CHECKPOINT; IC 50; M PHASE CELL CYCLE CHECKPOINT; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; TUMOR GROWTH; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; FEMALE; HETEROCYCLIC COMPOUNDS, 2-RING; HT29 CELLS; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; MICE, NUDE; MOLECULAR STRUCTURE; NEOPLASMS; POLYMERIZATION; SULFONAMIDES; TUBULIN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84886499582     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4011115     Document Type: Article

References (43)

1. Hamel, E. Antimitotic natural products and their interactions with tubulin Med. Res. Rev. 1996, 16, 207-231
2. Messaoudi, S.; Téguier, B.; Hamze, A.; Provot, O.; Peyrat, J. F.; De Losada, J. R.; Liu, J. M.; Bignon, J.; Wdzieczak-Bakala, J.; Thoret, S.; Dubois, J.; Brion, J. D.; Alami, M. Isocombretastatins A versus combretastatins A: the forgotten isoCA-4 isomer as a highly promising cytotoxic and antitubulin agent J. Med. Chem. 2009, 52, 4538-4542
3. Combes, S.; Barbier, P.; Douillard, S.; McLeer-Florin, A.; Bourgarel-Rey, V.; Pierson, J.-T.; Fedorov, A. Y.; Finet, J.-P.; Boutonnat, J.; Peyrot, V. Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins. Part 2 J. Med. Chem. 2011, 54, 3153-3162
4. Fortin, S.; Wei, L.; Moreau, E.; Lacroix, J.; Coîté, M. F.; Petitclerc, é.; Kotra, L. P.; C.-Gaudreault, R. Design, synthesis, biological evaluation, and structure-activity relationships of substituted phenyl 4-(2-oxoimidazolidin-1-yl)-benzenesulfonates as new tubulin inhibitors mimicking combretastatin A-4 J. Med. Chem. 2011, 54, 4559-4580
5. Gangjee, A.; Zhao, Y.; Lin, L.; Raghavan, S.; Roberts, E. G.; Risinger, A. L.; Hamel, E.; Mooberry, S. L. Synthesis and discovery of water-soluble microtubule targeting agents that bind to the colchicine site on tubulin and circumvent Pgp mediated resistance J. Med. Chem. 2010, 53, 8116-8128
6. Romagnoli, R.; Baraldi, P. G.; Andrea Brancale, A.; Ricci, A.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. Convergent synthesis and biological evaluation of 2-amino-4-(3',4',5'-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents J. Med. Chem. 2011, 54, 5144-5153
7. Flynn, B. L.; Gill, G. S.; Grobelny, D. W.; Chaplin, J. H.; Paul, D.; Leske, A. F; Lavranos, T. T.; Chalmers, D. K.; Charman, S. A.; Kostewicz, E.; Shackleford, D. M.; Morizzi, J.; Hamel, E.; Jung, K.; Kremmidiotis, G. Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)-benzo[ b ]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties J. Med. Chem. 2011, 54, 6014-6027
8. Flynn, B. L.; Hamel, E.; Jung, M. K. A one-pot synthesis of benzo[ b ]furan and indole inhibitors of tubulin polymerization J. Med. Chem. 2002, 45, 2670-2673
9. Dumontet, C.; Jordan, M. A. Microtubule-binding agents: a dynamic field of cancer therapeutics Nat. Rev. Drug Discovery 2010, 9, 790-803
10. Yoshino, H.; Ueda, N.; Niijima, J.; Sugumi, H.; Kotake, Y.; Koyanagi, N.; Yoshimatsu, K.; Asada, M.; Watanabe, T. Novel sulfonamides as potential, systemically active antitumor agents J. Med. Chem. 1992, 35, 2496-2497
11. Yoshimatsu, K.; Yamaguchi, A.; Yoshino, H.; Koyanagi, N.; Kitoh, K. Mechanism of action of E7010, an orally active sulfonamide antitumor agent: inhibition of mitosis by binding to the colchicine site of tubulin Cancer Res. 1997, 57, 3208-3213
12. Owa, T.; Yoshino, H.; Okauchi, T.; Yoshimatsu, K.; Ozawa, Y.; Sugi, N.; Nagasu, T.; Koyanagi, N.; Kitoh, K. Discovery of novel antitumor sulfonamides targeting G1 phase of the cell cycle J. Med. Chem. 1999, 42, 3789-3799
13. Ozawa, Y.; Sugi, N. H.; Nagasu, T.; Owa, T.; Watanabe, T.; Koyanagi, N.; Yoshino, H.; Kitoh, K.; Yoshimatsu, K. E7070, a novel sulphonamide agent with potent antitumour activity in vitro and in vivo Eur. J. Cancer 2001, 37, 2275-2282
14. Fukuoka, K.; Usuda, J.; Iwamoto, Y.; Fukumoto, H.; Nakamura, T.; Yoneda, T.; Narita, N.; Saijo, N.; Nishio, K. Mechanisms of action of the novel sulfonamide anticancer agent E7070 on cell cycle progression in human non-small cell lung cancer cells Invest New Drugs 2001, 19, 219-227
15. Tanaka, H.; Ohshima, N.; Ikenoya, M.; Komori, K.; Katoh, F.; Hidaka, H. HMN-176, an active metabolite of the synthetic antitumor agent HMN-214, restores chemosensitivity to multidrug-resistant cells by targeting the transcription factor NF-Y Cancer Res. 2003, 63, 6942-6947
16. Takagi, M.; Honmura, T.; Watanabe, S.; Yamaguchi, R.; Nogawa, M.; Nishimura, I.; Katoh, F.; Matsuda, M.; Hidaka, H. In vivo antitumor activity of a novel sulfonamide, HMN-214, against human tumor xenografts in mice and the spectrum of cytotoxicity of its active metabolite, HMN-176 Invest New Drugs 2003, 21, 387-399
17. DiMaio, M. A.; Mikhailov, A.; Rieder, C. L.; Von Hoff, D. D.; Palazzo, R. E. The small organic compound HMN-176 delays satisfaction of the spindle assembly checkpoint by inhibiting centrosome-dependent microtubule nucleation Mol. Cancer Ther. 2009, 8, 592-601
18. Chang, J. Y.; Hsieh, H. P.; Chang, C. Y.; Hsu, K. S.; Chiang, Y. F.; Chen, C. M.; Kuo, C. C.; Liou, J. P. 7-Aroyl-aminoindoline-1-sulfonamides as a novel class of potent antitubulin agents J. Med. Chem. 2006, 49, 6656-6659
19. Chang, J. Y.; Lai, M. J.; Chang, Y. T.; Lee, H. Y.; Cheng, Y. C.; Kuo, C. C.; Su, M. C.; Chang, C. Y.; Liou, J. P. Synthesis and biological evaluation of 7-arylindoline-1-benzenesulfonamides as a novel class of potent anticancer agents Med. Chem. Commun. 2010, 1, 152-155
20. Wang, T.; Zhang, Z.; Meanwell, N. A.; Kadow, J. F.; Yin, Z. Composition and Antiviral Activity of Substituted Azaindoleoxoacetic Piperazine Derivatives. WO02062423, 2002.
21. Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. The reaction of vinyl Grignard reagents with 2-substituted nitroarenes: a new approach to the synthesis of 7-substituted indoles Tetrahedron Lett. 1989, 30, 2129-2132
22. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 1995, 95, 2457-2483
23. Liou, J. P.; Hsu, K. S.; Kuo, C. C.; Chang, C. Y.; Chang, J. Y. A novel oral indoline-sulfonamide agent, J30, exhibits potent activity against human cancer cells in vitro and in vivo through the disruption of microtubule J. Pharmacol. Exp. Ther. 2007, 323, 398-405
24. Kuo, C. C.; Hsieh, H. P.; Pan, W. Y.; Chen, C. P.; Liou, J. P.; Lee, S. J.; Chang, Y. L.; Chen, L. 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
25. Nien, C. Y.; Chen, Y. C.; Kuo, C. C.; Hsieh, H. P.; Chang, C. Y.; Wu, J. S.; Wu, S. Y.; Liou, J. P.; Chang, J. Y. 5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors J. Med. Chem. 2010, 53, 2309-2313
26. Cai, S. X. Small molecule vascular disrupting agents: potential new drugs for cancer treatment Recent Pat. Anti-Cancer Drug Discovery 2007, 2, 79-101
27. Pettit, G. R.; Temple, C. J.; Narayanan, V. L.; Varma, R.; Simpson, M. J.; Boyd, M. R.; Rener, G. A.; Bansal, N. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs Anti-Cancer Drug Des. 1995, 10, 299-309
28. Dark, G. G.; Hill, S. A.; Prise, V. E.; Tozer, G. M.; Pettit, G. R.; Chaplin, D. J. Combretastatin A-4, an agent that displays potent and selective toxicity toward tumor vasculature Cancer Res. 1997, 57, 1829-1834
29. Siemann, D. W.; Bibby, M. C.; Dark, G. G.; Dicker, A. P.; Eskens, F. A. L. M.; Horsman, M. R.; Marme, D.; LoRusso, P. M. Differentiation and definition of vascular-targeted therapies Clin. Cancer Res. 2005, 11, 416-420
30. Tozer, G. M.; Kanthou, C.; Baguley, B. C. Disrupting tumour blood vessels Nat. Rev. Cancer 2005, 5, 423-435
31. Patterson, D. M.; Rustin, G. J. S. Vascular damaging agents Clin. Oncol. 2007, 19, 443-456
32. Tozer, G. M.; Akerman, S.; Cross, N. A.; Barber, P. R.; Björndahl, M. A.; Greco, O.; Harris, S.; Hill, S. A.; Honess, D. J.; Ireson, C. R.; Pettyjohn, K. L.; Prise, V. E.; Reyes-Aldasoro, C. C. Blood vessel maturation and response to vascular-disrupting therapy in single vascular endothelial growth factor-A isoform-producing tumors Cancer Res. 2008, 68, 2301-2311
33. Siemann, D. W.; Chaplin, D. J.; Walicke, P. A. A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA-4P) Expert Opin. Invest. Drugs 2009, 18, 189-197
34. 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, 6595-6602
35. Kremmidiotis, G.; Leske, A. F.; Lavranos, T. C.; Beaumont, D.; Gasic, J.; Hall, A.; O'Callaghan, M.; Matthews, C. A.; Flynn, B. BNC105: a novel tubulin polymerization inhibitor that selectively disrupts tumor vasculature and displays single-agent antitumor efficacy Mol. Cancer Ther. 2010, 9, 1562-1573
36. Finlay, G. J.; Baguley, B. C.; Wilson, W. R. A semiautomated microculture method for investigating growth inhibitory effect of cytotoxic compounds on exponentially growing carcinoma cells Anal. Biochem. 1984, 139, 272-277
37. Kuo, C. C.; Hsieh, H. P.; Pan, W. Y.; Chen, C. P.; Liou, J. P.; Lee, S. J.; Chang, Y. L.; Chen, L. 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
38. Liou, J. P.; Chang, J. Y.; Chang, C. W.; Chang, C. Y.; Mahindroo, N.; Kuo, F. M.; Hsieh, H. P. Synthesis and structure-activity relationships of 3-aminobenzophenones as antimitotic agents J. Med. Chem. 2004, 47, 2897-2905
39. Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Epothilones, a new class of microtubule-stabilizing agents with a Taxol-like mechanism of action Cancer Res. 1995, 55, 2325-2333
40. Tahir, S. K.; Kovar, P.; Rosenberg, S. H.; Ng, S. C. Rapid colchicine competition-binding scintillation proximity assay using biotin-labeled tubulin BioTechniques 2000, 29, 156-160
41. Tahir, S. K.; Han, E. K.; Credo, B.; Jae, H. S.; Pietenpol, J. A.; Scatena, C. D.; Wu-Wong, J. R.; Frost, D.; Sham, H.; Rosenberg, S. H.; Ng, S. C. A-204197, a new tubulin-binding agent with antimitotic activity in tumor cell lines resistant to known microtubule inhibitors Cancer Res. 2001, 61, 5480-5485
42. Tahir, S. K.; Nukkala, M. A.; Zielinski Mozny, N. A.; Credo, R. B.; Warner, R. B.; Li, Q.; Woods, K. W.; Claiborne, A.; Gwaltney, S. L., II; Frost, D. J.; Sham, H. L.; Rosenberg, S. H.; Ng, S. C. Biological activity of A-289099: an orally active tubulin-binding indolyloxazoline derivative Mol. Cancer Ther. 2003, 2, 227-233
43. Cheng, Y.; Prusoff, W. H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 percent inhibition (I50) of an enzymatic reaction Biochem. Pharmacol. 1973, 22, 3099-3108