Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: Synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 14, 2006, Pages 4750-4760

  Yonetoku, Yasuhiro ^a   Kubota, Hirokazu ^a   Okamoto, Yoshinori ^a   Toyoshima, Akira ^a   Funatsu, Masashi ^a   Ishikawa, Jun ^a   Takeuchi, Makoto ^a   Ohta, Mitsuaki ^a   Tsukamoto, Shin ichi ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

Anti inflammatory; Ca2+ release activated Ca2+ channel; Channel inhibitors; CRAC channel; Interleukin 2; Quantitative structure activity relationship

Indexed keywords

(1 METHYL 1H PYRROL 2 YL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; (4 BROMOPHENYL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; (4 CHLOROPHENYL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; (4 CYANOPHENYL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; (4 DIMETHYLAMINOPHENYL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; (4 FLUOROPHENYL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; (4 ISOPROPYLPHENYL) 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE; 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBONYLCHLORIDE; 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXAMIDE DERIVATIVE; 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXYLIC ACID; 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) N (4 NITROPHENYL) 2 THIOPHENECARBOXAMIDE; 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYTRAZOL 5 YL) N (PYRIDIN 4 YL) 2 THIOPHENECARBOXAMIDE; CALCIUM ANTAGONIST; CONCANAVALIN A; ETHYL 5 (1 METHYL 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL) 2 THIOPHENECARBOXYLATE; INTERLEUKIN 2; PHYTOHEMAGGLUTININ; UNCLASSIFIED DRUG; VOLTAGE GATED CALCIUM CHANNEL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; FEMALE; MOUSE; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS; DRUG EVALUATION, PRECLINICAL; FEMALE; HUMANS; INTERLEUKIN-2; JURKAT CELLS; MICE; MICE, INBRED BALB C; PC12 CELLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; THIOPHENES;

EID: 33646821317     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.03.024     Document Type: Article

References (46)

1. Mori Y., Mikala G., Varadi G., Kobayashi T., Koch S., Wakamori M., and Schwartz A. Jpn. J. Pharmacol. 72 (1996) 83
2. For example:. Takami T., and Shigemasa M. Hypertens. Res. 26 (2003) 609
3. For example:. Jouvenceau A., Eunson L.H., Spauschus A., Ramesh V., Zuberi S.M., Kullmann D.M., and Hanna M.G. Lancet 358 (2001) 801
4. Hoth M. Pflügers Arch. 430 (1995) 315
5. Hoth M., and Penner R. Nature 355 (1992) 353
6. Lewis R.S., and Cahalan M.D. Annu. Rev. Immunol. 13 (1995) 623
7. Clementi E., and Meldolesi J. Cell Calcium 19 (1996) 269
8. Geiszt M., Kapus A., Nemet K., Farkas L., and Ligeti E. J. Biol. Chem. 272 (1997) 26471
9. Clapham D.E. Cell 80 (1995) 259
10. Petersen O.H., Gerasimenko O.V., Gerasimenko J.V., Mogami H., and Tepikin A.V. Cell Calcium 23 (1998) 87
11. Berridge M.J., and Irvine R.F. Nature 341 (1989) 197
12. Putney Jr. J.W. Cell Calcium 11 (1990) 611
13. Randriamampita C., and Tsien R.Y. Nature 364 (1993) 809
14. Fasolato C., Innocenti B., and Pozzan T. Trends Pharmacol. Sci. 15 (1994) 77
15. Berridge J.M. Biochem. J. 312 (1995) 1
16. Fanger C.M., Hoth M., Crabtree G.R., and Lewis R.S. J. Cell Biol. 131 (1995) 655
17. Zweifach A., and Lewis R.S. J. Biol. Chem. 270 (1995) 14445
18. Zweifach A., and Lewis R.S. J. Gen. Physiol. 107 (1996) 597
19. Slaughter R.S., Garcia M.L., and Kaczorowski G.J. Curr. Pharm. Design 2 (1996) 610
20. Cahalan M.D., and Chandy K.G. Curr. Opin. Biotechnol. 8 (1997) 749
21. Chung S.C., McDonald T.V., and Gardner P. Br. J. Pharmacol. 113 (1994) 861
22. Encabo A., Romanin C., Birke F.W., Kukovets W.R., and Groschner K. Br. J. Pharmacol. 119 (1996) 702
23. Felder C.C., Ma A.L., Liotta L.A., and Kohn E.C. J. Pharm. Exp. Ther. 257 (1991) 967
24. Kubota H., Yonetoku Y., Sugasawa K., Funatsu M., Kawazoe S., Toyoshima A., Okamoto Y., Ishikawa J., Takeuchi M. WO 9919303; Chem. Abstr. 1999, 130, 311815.
25. Reid J.C., and Calvin M. J. Am. Chem. Soc. 72 (1950) 2948
26. Mach R.H., Leudtke R.R., Unsworth C.D., Boundy V.A., Nowak P.A., Scripko J.G., Elder S.T., Jackson J.R., Hoffman P.L., Evora P.H., Rao A.V., Molinoff P.B., Childers S.R., and Ehrenkaufer R.L. J. Med. Chem. 36 (1993) 3707
27. Ref. 7.
28. Timmerman L.A., Clipstone N.A., Ho S.N., Northrop J.P., and Crabtree G.R. Nature 383 (1996) 837
29. Virgilio F.D., Milani D., Leon A., Meldolesi J., and Pozzan T. J. Biol. Chem. 262 (1987) 9189
30. Fujita T., Iwasa J., and Hansch C. J. Am. Chem. Soc. 86 (1964) 5175
31. Iwasa J., Fujita T., and Hansch C. J. Med. Chem. 8 (1965) 153
32. Hansch C., and Calef D.F. J. Org. Chem. 41 (1976) 1240
33. Swain C.G., and Lupton E.C. J. Am. Chem. Soc. 90 (1968) 4328
34. Hansch C., Leo A., Uner S.H., Kim K.H., Nikaidani D., and Lien E.J. J. Med. Chem. 16 (1973) 1207
35. Chapman N. B., Shorter J., Eds.; Advances in Linear Free Energy Relationship, Plenium Press: London, 1972.
36. Chapman N. B., Shorter J., Eds.; Correlation Analysis in Chemistry, Plenium Press: London, 1978.
37. Taft R.W. In: Newman M.S. (Ed). Steric Effects in Organic Chemistry (1956), Wiley, New York 556
38. Kutter E., and Hansch C. J. Med. Chem. 12 (1969) 647
39. Fujita T. J. Med. Chem. 16 (1973) 923
40. Verloop A., Hoogenstraaten W., Tipker J. In Drug Design, Ariens, E. A., Ed.; Academic Press: New York, 1976; Vol. 7, pp 165.
41. Verloop A. Pesticide Chemistry, In Human Welfare and the Environment, Miyamoto, J., Kearney, P. C., Eds.; Pergamon Press: Oxford, 1983; Vol. 1, pp 339.
42. Iwamura H. In Kozokassei Sokan to Drug Design, Fujita, T., Ed.; Kagaku Zokan, Kagaku Dojin: Kyoto, 1986; Vol. 107, pp 79.
43. ACD/log P DB program, ver. 3.5 for Microsoft Windows, LA systems Corp.
44. Tiegs G., Hentschel J., and Wendel A. J. Clin. Invest. 90 (1992) 196
45. De Rosa M., Issac R.P., and Houghton G. Tetrahedron Lett. 36 (1995) 9261
46. Binder D., Habison G., and Noe C.R. Synthesis 4 (1977) 255