Novel retinoic acid receptor α agonists: Syntheses and evaluation of pyrazole derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 7, 2000, Pages 619-622

  Kikuchi, Kouichi ^a   Hibi, Shigeki ^a   Yoshimura, Hiroyuki ^a   Tai, Kenji ^a   Hida, Takayuki ^a   Tokuhara, Naoki ^a   Yamauchi, Toshihiko ^a   Nagai, Mitsuo ^a  

^a EISAI CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 N TERT BUTYL 5 ISOPROPYLPYRAZOLE DERIVATIVE; 1 TRIFLUOROETHYL 5 ISOPROPYLPYRAZOLE DERIVATIVE; 4 [5 (1,5 DIISOPROPYL 1H 3 PYRAZOLYL) 1H 2 PYRROLYL]BENZOIC ACID; PYRAZOLE DERIVATIVE; RETINOIC ACID; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CELL DIFFERENTIATION; CELL STRAIN HL 60; CHEMICAL MODIFICATION; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; TRANSACTIVATION;

BINDING, COMPETITIVE; CELL DIFFERENTIATION; HL-60 CELLS; HUMANS; PYRAZOLES; RECEPTORS, RETINOIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034599594     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00066-4     Document Type: Article

References (31)

1. Mangelsdorf, D. J.; Umesono, K.; Evans, R. M. In The Retinoids; Sporn, M. B.; Roberts, A. B.; Goodman, D. S., Eds; Raven Press: New York, 1994.
2. Leid, M.; Kastner, P.; Chambon, P. Trends Biochem. Sci. 1992, 17, 427; and references cited therein.
3. (a) Orfanos, C. E.; Ehlert, R.; Gollnick, H. Drugs 1987, 34, 459; and references cited therein.
4. (b) Orfanos, C. E.; Zouboulis, C. C.; Almond-Roesler, B.; Geilen, C. C. Drugs 1997, 53, 358; and references cited therein.
5. (a) Smith, M. A.; Parkinson, D. R.; Cheson, B. D.; Friedman, M. A. J. Clin. Oncol. 1992, 10, 839.
6. (b) Yokes, E. E.; Weichselbaum, R. R.; Lippman, S. M.; Hong, W. K. N. Engl. J. Med. 1993, 328, 184.
7. (c) Nagpal, S.; Chandraratna, R. A. S. Curr. Pharm. Des. 1996, 2, 295; and references cited therein.
8. (d) Lotan, R. FASEB J. 1996, 10, 1031; and references cited therein.
9. (e) Hong, W. K.; Sporn, M. B. Science 1997, 278, 1073; and references cited therein.
10. (a) Amstrong, R. B.; Ashenfelter, K. O.; Eckhoff, C.; Levin, A. A.; Shapio, S. S. In The Retinoids: Sporn, M. B.; Roberts, A. B.; Goodman, D. S., Eds; Raven Press: New York, 1994, pp 545-572.
11. (b) Standeven, A. M.; Beard, R. L.; Johnson, A. T. Boehm, M. F.; Escobar, M.; Heyman, R. A; Chandraratna, R. A. S. Fundam. Appl. Toxicol. 1996, 33, 264.
12. (c) Soprano, D. R.; Soprano, K. J. Annu. Rev. Nutr. 1995, 15, 111; and references cited therein.
13. (d) Willhite, C. C.; Dawson, M. I. Toxicol. Appl. Pharmacol. 1990, 103, 324.
14. (a) Kagechika, H.; Kawachi, E.; Hashimoto, Y.; Himi, T.; Shudo, K. J. Med. Chem. 1988, 31, 2182.
15. (b) Teng, M.; Duong, T. T.; Klein, E. S.; Chandraratna, R. A. S. J. Med. Chem. 1996, 39, 3035.
16. (c) Johnson, A. T; Klein, E. S. Wang, L; Pino, M. E; Chandraratna, R. A. S. J. Med. Chem. 1996, 39, 5027.
17. (d) Esgleyes-Ribot, T.; Chandraratna, R. A. S.; Lew-Kaya, D.; Sefton, J.; Duvic, M. J. J. Am. Acad. Dermatol. 1994, 30, 581.
18. (e) Delescluse, C.; Cavey, M. T.; Martin, B.; Bernard, B. A.; Reichert, U.; Maignan, J.; Darmon, M.; Shroot, B. Mol. Pharmacol. 1991, 40, 556.
19. (f) Charpentier, B.; Bernardon, J-M.; Eustache, J.; Millois, C.; Martin, B.; Michel, S.; Shroot, B. J. Med. Chem. 1995, 38, 4993.
20. (g) Yu, K.-L.; Spinazze, P.; Ostrowski, J.; Currier, S. J.; Pack, E. J.; Hammer, L.; Roalsvig, T.; Honeyman, J. A.; Tortolani, D. R.; Reczek, P. R.; Mansuri, M. M.; Starret, J. E., Jr. J. Med. Chem. 1996, 39, 2411
21. Tobita, T.; Takeshita, A.; Kitamura, K.; Ohnishi, K.; Yanagi, M.; Hiraoka, A.; Karasuno, T.; Takeuchi, M.; Miyawaki, S.; Ueda, R.; Naoe, T.; Ohno, R. Blood 1997, 90, 967.
22. (a) Ishibashi, Y.; Harada, S.; Ohkawara, A.; Tagami, H.; lizuka, H.; Toda, K.; Takigawa, M.; Shimizu, M.; Nakashima, M. Rinshouiyaku 1995, 11, 721.
23. (b) Ishibashi, Y. Rinshouiyaku 1995, 11, 733.
24. Kuwabara, K.; Shudo, K.; Hori, Y. FEBS Letters 1996, 378, 153.
25. (a) Yoshimura, H.; Nagai, M.; Hibi, S.; Kikuchi, K.; Abe, S.; Hida, T; Higashi, S.; Hishinuma, I.; Yamanaka, T. J. Med. Chem. 1995, 38, 3163.
26. (b) Hibi, S.; Kikuchi, K.; Yoshimura, H.; Nagai, M.; Tai, K.; ; Hida, T. J. Med. Chem. 1998, 41, 3245.
27. (c) Kikuchi, K.; Hibi, S.; Yoshimura, H.; Tokuhara, N.; Tai, K.; Hida, T.; Yamauchi, T.; Nagai, M. J. Med. Chem. 2000, 43, 409.
28. Barrero, A. F.; Sanchez, J. F.; Oltra, J. E.; Teva, D.; Ferrol, R. R.; Elmerabet, J.; Del Moral, R. G.; Lucena, M. A.; O'Valle, F. Eur. J. Med. Chem. 1994, 29, 773.
29. Regiochemistry of these pyrazole derivative was estimated from proton NMR and Rf values, compared with those of similar pyrazole derivatives: Nicolai, E.; Cure, G.; Goyard, J.; Kirchner, M.; Teulon, J-M.; Versigny, A.; Cazes, M.; Virone-Oddos, A.; Caussade, F.; Cloarrec, A. Chem. Pharm. Bull. 1994, 42, 1617. The structures of 11b and 11c were supported by a 2D NOESY experiment, in which the NOE was observed between the methyne proton on the 5-position isopropyl and the methyne proton on the 1-position isopropyl or the t-butyl protons on the 1-position, respectively.
30. Goto, M.; Yamada, K.; Katayama, K.; Tanaka, I. Mol. Pharmacol. 1996, 49, 860.
31. Boehm, M. F.; Zhang, L.; Zhi, L.; McClung, M. R.; Berger, E.; Wagoner, M.; Mais, D. E.; Suto, C. M.; Davies, P. J. A.; Heyman, R. A.; Nadzan, A. M. J. Med. Chem. 1995, 38, 314.