[4-(Imidazol-1-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

Journal of Medicinal Chemistry

Volumn 49, Issue 19, 2006, Pages 5769-5776

  Mahboobi, Siavosh ^a   Sellmer, Andreas ^a   Höcher, Heymo ^a   Eichhorn, Emerich ^a   Bär, Thomas ^b   Schmidt, Mathias ^b   Maier, Thomas ^b   Stadlwieser, Josef F ^b   Beckers, Thomas L ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b ALTANA PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

[4 (IMIDAZOL 1 YL)THIAZOL 2 YL]PHENYLAMINE DERIVATIVE; ANILINE DERIVATIVE; COLCHICINE; CYCLIN DEPENDENT KINASE INHIBITOR 1B; IMATINIB; TUBULIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING COMPETITION; BINDING SITE; CANCER CELL CULTURE; CELL CYCLE G1 PHASE; COLON CARCINOMA; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; INHIBITION KINETICS; MICROTUBULE; MICROTUBULE ASSEMBLY; MITOSIS INHIBITION; PHENOTYPE; PROTEIN EXPRESSION; TARGET CELL;

ANILINE COMPOUNDS; BINDING SITES; CELL LINE, TUMOR; CELL SHAPE; CELL SURVIVAL; COLCHICINE; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; TUBULIN; TUBULIN MODULATORS;

EID: 33748868675     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060545p     Document Type: Article

References (27)

1. Beckers, T.; Mahboobi, S. Natural, semisynthetic and synthetic microtuble inhibitors for cancer therapy. Drugs Future 2003, 28, 767-785.
2. Swanton, C. Cell-cyle targeted therapies. Lancet Oncol. 2004, 5, 27-36.
3. Byth, K. F.; Cooper, N.; Culshaw, J. D.; Heaton, D. W.; Oakes, S. E.; Minshull, C. A.; Norman, R. A.; Pauptit, R. A.; Tucker, J. A.; Breed, J.; Pannifer, A.; Rowsell, S.; Stanway, J. J.; Valentine, A. L.; Thomas, A. P. Imidazo[1,2-b]pyridazines: a potent and selektive class of cyclin-dependent kinase inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 2249-2252.
4. Schwartz, G. K.; Shah, M. A. Targeting the cell cycle: a new approach to cancer therapy. J. Clin. Oncol. 2005, 23, 9408-9421.
5. Rasmussen, C. R.; Villani, F. J.; Weaner, L. E.; Reynolds, B. E.; Hood, A. R.; Hecker, L. R.; Nortey, S. O.; Hanslin, A.; Costanzo, M. J.; Powell, E. T.; Molinari, A. J. Improved procedures for the preparation of cycloalkyl-, arylalkyl-, and arylthioureas. Synthesis 1988, 6, 456-459.
6. Brown, M. L.; Cheung, M.; Dickerson, S. H.; Gauthier, C.; Harris, P. A.; Hunter, R. N.; Pacofsky, G.; Peel, M. R.; Stafford, J. A. Preparation of 1,3-oxazol-2-amines as VEGFR2, CDK2, and CDK4 inhibitors. PCT WO 2004/032882 A2, 2004.
7. Khodair, A. I. A convenient synthesis of 2-arylidene-5H-thiazolo-[2,3-b] quinazoline-3,5[2H]-diones and their benzoquinolone derivatives. J. Heterocycl. Chem. 2002, 39, 1153-1160.
8. 2- thiazolin-4-ones. Pharmazie 1981, 36, 862-863.
9. Schmidt, M.; Lu, Y.; Liu, B.; Fang, M.; Mendelsohn, J.; Fan, Z. Differential modulation of paclitaxel-mediated apoptosis by p21 waf1 and p27kip1. Oncogene 2000, 19, 2423-2429.
10. Schmidt, M.; Lu, Y.; Parant, J. M.; Lozano, G.; Bacher, G.; Beckers, T. Differential roles of p21(Aaf1) and p27(Kip1) in modulating chemosensitivity and their possible application in drug discovery studies. Mol. Pharmacol. 2001, 60, 900-906.
11. Tahir, S. K.; Kovar, P.; Rosenberg, S. H. Rapid colchicine competition binding scintillation proximity assay using biotin-labeled tubulin. BioTechniques 2000, 29, 156-160.
12. Bacher, G.; Bernd, N.; Peter, E.; Udo, V.; Siegfried, S.; Alexei, S.; Thomas, K.; Thomas, B. D-24851, a novel synthetic microtubule inhibitor, exerts curative antitumoral activity in vivo, shows efficacy toward multidrug-resistant tumor cells, and lacks neurotoxicity. Cancer Res. 2001, 61, 392-399.
13. Mahboobi, S.; Pongratz, H.; Hufsky, H.; Hockemeyer, J.; Frieser, M.; Lyssenko, A.; Paper, D. H.; Bürgermeister, J.; Böhmer, F.-D.; Fiebig, H.-H.; Burger, A. M.; Baasner, S.; Beckers, T. Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents. J. Med. Chem. 2001, 44, 4535-4553.
14. Byth, K. F.; Culshaw, J. D.; Green, S.; Oakes, S. E.; Thomas, A. P. Imidazo[1,2-a]pyridines. Part 2: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 2245-2248.
15. Siebert, C. D. Arzneistoffentwicklung - Das Bioisosteriekonzept. Chem. Unserer Zeit 2004, 38, 320-324.
16. Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Glivec (STI571, imatinib), a rationally developed, targeted anticancer drug. Nat. Rev. Drug Discovery 2002, 1, 493-502.
17. Kinet, J.-P.; Moussy, A. Use of tyrosin kinase inhibitors for treating cerebral ischemia. PCT WO 2004/096225 A2, 2004.
18. Ciufolini, M.; Wermuth, C.; Gielthen, B.; Moussy, A. Preparation of 2-(3-aminoaryl)amino-4-aryl-thiazoles as tyrosin phosphokinase c-Kit inhibitors. PCT WO 2004/014903 A1, 2004.
19. Beckers, T.; Reissmann, T.; Schmidt, M.; Burger, A. M.; Fiebig, H. H.; Vanhoefer, U.; Pongratz, H.; Hufsky, H.; Hockemeyer, J.; Frieser, M.; Mahboobi, S. 2-Aroylindoles, a novel class of potent, orally active small molecule tubulin inhibitors. Cancer Res. 2002, 62, 3113-3119.
20. O'Brian, J.; Wilson, I.; Orton, T.; Pognan, F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell toxicity. Eur. J. Biochem. 2000, 267, 5421-5426.
21. Ramsh, S. M.; Ginak, N. A.; Sochilin, E. G. Study of the reactivity and tautomerism of azolidines. XXVII. Study of 2-(arylimino)-thiazolidin-4-one tautomerism by UV and IR spectroscopy. Zh. Org. Khim. 1979, 15, 1506-1513.
22. Pawar, R. A.; Rajput, A. P. Studies on the Vilsmeier-Haack reaction. A versatile new synthesis of 4-chloro-2-phenylaminothiazole-5-carboxaldehyde and related fused heterocyclic compounds and heterocyclic Schiffs bases. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989, 28, 866-867.
23. Pohloudek-Fabini, R.; Schroepl, E. Acid isothiocyanates. III. Acid isothiocyanate conversion to unsymmetric, disubstituted acylthioureas with aromatic amines. 2. Pharmazie 1968, 23, 561-566.
24. Pohloudek-Fabiani, R.; Schroepl, E. Acid isothiocyanates. III. Acid isothiocyanate conversion to unsymmetric, disubstituted acylthioureas with aromatic amines. 2. Pharmazie 1968, 23, 561-566.
25. Rao, R. P. Thiazolidinones and thiazolidinediones as fungicidal agents. Indian J. Appl. Chem. 1960, 23, 110.
26. Singh, A.; Uppal, A. S. Structure of acylated 4-aminothiazolines: Part XII. Studies in 4-aminothiazolines. Indian J. Chem., Section B: Org. Chem. Incl. Med. Chem. 1978, 16, 779-781.
27. Ganapathi, K. Chemotherapy of bacterial infections. III. Synthesis of N4-amino-substituted heterocyclic derivatives of sulfanilamide. Proc.-Indian Acad. Sci., Sect. A 1940, 12, 278-283.