Dicarba-closo-dodecaboranes as a pharmacophore. Retinoidal antagonists and potential agonists

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 3, 1999, Pages 398-404

  Iijima, Toru ^a   Endo, Yasuyuki ^a   Tsuji, Motonori ^a   Kawachi, Emiko ^a   Kagechika, Hiroyuki ^a   Shudo, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Boron neutron capture therapy; Carborane; Dicarba closo dodecaborane; Differentiation; Retinoid

Indexed keywords

CARBORANE DERIVATIVE; DICARBA CLOSO DODECABORANE; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

AGONIST; ARTICLE; BINDING AFFINITY; CELL DIFFERENTIATION; CELL STRAIN HL 60; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBICITY; NEUTRON CAPTURE THERAPY; RECEPTOR DENSITY; STRUCTURE ACTIVITY RELATION;

EID: 0032922026     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.398     Document Type: Article

References (31)

1. Hawthorne M. F., Angew. Chem., Int. Ed. Engl., 32, 950-984 (1993); Slatkin D. N., Brain, 114, 1609-1629 (1991).
2. Hawthorne M. F., Angew. Chem., Int. Ed. Engl., 32, 950-984 (1993); Slatkin D. N., Brain, 114, 1609-1629 (1991).
3. For a recent review see: Soloway A. H., Tjarks W., Barnum B. A., Rong F.-G., Barth R. F., Codogni I. M., Wilson J. G., Chem. Rev., 98, 1515-1562 (1998).
4. Yamamoto Y., Seko T., Nakamura H., Nemoto H., Hojo H., Nukai N., Hashimoto Y., J. Chem. Soc. Chem. Commun., 1992, 157-158; Tjarks W., Anisuzzaman A. K. M., Liu L., Soloway A. H., Barth R. F., Perkins D. J., Adams D. M., J. Med. Chem., 35, 1628-1631 (1992).
5. Yamamoto Y., Seko T., Nakamura H., Nemoto H., Hojo H., Nukai N., Hashimoto Y., J. Chem. Soc. Chem. Commun., 1992, 157-158; Tjarks W., Anisuzzaman A. K. M., Liu L., Soloway A. H., Barth R. F., Perkins D. J., Adams D. M., J. Med. Chem., 35, 1628-1631 (1992).
6. Leukart O., Caviezel M., Eberle A., Escher E., Tun-Kyi A., Schwyzer R., Helv. Chim. Acta, 59, 2184-2187 (1976); Wyzlic I. M., Soloway A. H., Tetrahedron Lett., 33, 7489-7492 (1992); Radel P. A., Kahl A. B., J. Og. Chem., 61, 4582-4588 (1996).
7. Leukart O., Caviezel M., Eberle A., Escher E., Tun-Kyi A., Schwyzer R., Helv. Chim. Acta, 59, 2184-2187 (1976); Wyzlic I. M., Soloway A. H., Tetrahedron Lett., 33, 7489-7492 (1992); Radel P. A., Kahl A. B., J. Og. Chem., 61, 4582-4588 (1996).
8. Leukart O., Caviezel M., Eberle A., Escher E., Tun-Kyi A., Schwyzer R., Helv. Chim. Acta, 59, 2184-2187 (1976); Wyzlic I. M., Soloway A. H., Tetrahedron Lett., 33, 7489-7492 (1992); Radel P. A., Kahl A. B., J. Og. Chem., 61, 4582-4588 (1996).
9. Miura M., Gabel D., Oenbrink G., Fairchild R. G., Tetrahedron Lett., 31, 2247-2250 (1990).
10. Davis M. A., Soloway A. H., J. Med. Chem., 10, 730-732 (1967); Kelly D. P., Bateman S. A., Martin R. F., Reum M. E., Rose M., Whittaker A. D., Aust. J. Chem., 47, 247-262 (1994); Yamamoto Y., Cai J., Nakanura H., Sadayori N., Nemoto H., J. Org. Chem., 60, 3352- 3357 (1995).
11. Davis M. A., Soloway A. H., J. Med. Chem., 10, 730-732 (1967); Kelly D. P., Bateman S. A., Martin R. F., Reum M. E., Rose M., Whittaker A. D., Aust. J. Chem., 47, 247-262 (1994); Yamamoto Y., Cai J., Nakanura H., Sadayori N., Nemoto H., J. Org. Chem., 60, 3352- 3357 (1995).
12. Davis M. A., Soloway A. H., J. Med. Chem., 10, 730-732 (1967); Kelly D. P., Bateman S. A., Martin R. F., Reum M. E., Rose M., Whittaker A. D., Aust. J. Chem., 47, 247-262 (1994); Yamamoto Y., Cai J., Nakanura H., Sadayori N., Nemoto H., J. Org. Chem., 60, 3352-3357 (1995).
13. Sweet F., Steroids, 37, 223-238 (1981); Sweet F., Samant B. R., "Synthesis and Application of Isotope Labeled Compounds" ed. by Ducan W. P., Susa A. B., Elsevier: Amsterdam, 1982, p. 175.
14. Sweet F., Steroids, 37, 223-238 (1981); Sweet F., Samant B. R., "Synthesis and Application of Isotope Labeled Compounds" ed. by Ducan W. P., Susa A. B., Elsevier: Amsterdam, 1982, p. 175.
15. Bregradze V. I., Chem. Rev., 92, 209-223 (1992).
16. Cunliffe W. J., Miller, A. J., Eds., "Retinoid Therapy", MTP Press Ltd., Lancaster, 1984; Bollag W., Holdener E. E., Ann. Oncol., 3, 513-526 (1992).
17. Cunliffe W. J., Miller, A. J., Eds., "Retinoid Therapy", MTP Press Ltd., Lancaster, 1984; Bollag W., Holdener E. E., Ann. Oncol., 3, 513-526 (1992).
18. Sporn M. B., Roberts A. B., Goodman D. S., Eds., "The Retinoids," 2nd ed., Raven Press, New York, 1994.
19. Evans R. M., Science, 240,889-895 (1988).
20. Shudo K., Kagechika H., Adv. Drug Res., 24, 81-119 (1993).
21. Bourguet W., Ruff M., Chambon P., Gronemeyer H., Moras D., Nature (London), 375, 377-382 (1995); Renaud J.-P., Rochel N., Ruff M., Vivat V, Chambon P., Gronemeyer H., Moras D., ibid. 378, 681-689 (1995).
22. Bourguet W., Ruff M., Chambon P., Gronemeyer H., Moras D., Nature (London), 375, 377-382 (1995); Renaud J.-P., Rochel N., Ruff M., Vivat V, Chambon P., Gronemeyer H., Moras D., ibid. 378, 681-689 (1995).
23. Darmon M., Rocher M., Cavey M. T., Nartin B., Rabilloud T., Delescluse C., Shroot B., Skin Pharmacol., 1, 161-175 (1988).
24. Kaneko S., Kagechika H., Kawachi E., Hashimoto Y., Shudo K., Med. Chem. Res., 1, 220-225 (1991).
25. Hawthorne M. F., Berry T. E., Wegner P. A., J. Am. Chem. Soc., 87, 4746-4750 (1965).
26. Scobie M., Threadgill M. D., J. Chem. Soc. Perkin Trans, 1, 1994, 2059-2063.
27. The icosahedral cage carbon atoms are generally found in an electron-deficient system. The electronic bonding structure of the two cage carbons in the carboranes still remains ambiguous. Wu S.-H., Jones M., Inorg. Chem., 27, 2005-2008 (1988) . The substituents at the 2-position of the carborane influence the orientation of the plane of the phenyl ring relative to the C-C in the cage. Crystallographic analysis of 1- phenyl-2-alkyl-1,2-carboranes has been reported. Brain P. T., Cowie, J., Donohoe D. J., Hnyk D., Rankin D. W. H., Reed D., Reid B. D., Robertson H. E., Welch A. J., ibid., 35, 1701-1708 (1996).
28. The icosahedral cage carbon atoms are generally found in an electron- deficient system. The electronic bonding structure of the two cage carbons in the carboranes still remains ambiguous. Wu S.-H., Jones M., Inorg. Chem., 27, 2005-2008 (1988) . The substituents at the 2-position of the carborane influence the orientation of the plane of the phenyl ring relative to the C-C in the cage. Crystallographic analysis of 1-phenyl-2-alkyl-1,2-carboranes has been reported. Brain P. T., Cowie, J., Donohoe D. J., Hnyk D., Rankin D. W. H., Reed D., Reid B. D., Robertson H. E., Welch A. J., ibid., 35, 1701-1708 (1996).
29. Austin W. B., Bilow N., Kelleghan J., Lau K. S., J. Org. Chem., 46, 2280-2286 (1981).
30. Collins S. J., Ruscetti F. W., Gallagher R. E., Gallo R. C., J. Exp. Med., 149, 964-974 (1979).
31. Umemiya H., Fukasawa H., Ebisawa M., Eyrolles L., Kawachi E., Eisenmann G., Gronemeyer H., Hashimoto Y., Shudo K., Kagechika H., J. Med. Chem., 40, 4222-4234 (1997).