Structural development of liver X receptor (LXR) antagonists derived from thalidomide-related glucosidase inhibitors

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 12, 2007, Pages 1750-1754

  Noguchi Yachide, Tomomi ^a   Miyachi, Hiroyuki ^a   Aoyama, Hiroshi ^a   Aoyama, Atsushi ^a   Makishima, Makoto ^b   Hashimoto, Yuichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b NIHON UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Antagonist; Glucosidase inhibitor; Liver X receptor; Phthalimide skeleton; Thalidomide

Indexed keywords

5 CHLORO N 2' N PENTYLPHENYL 2,3 DIHYDROISOINDOLE 1,3 DITHIONE; 5 CHLORO N 2' N PENTYLPHENYLPHTHALIMIDE; 5 CHLORO N 2' PENTYLPHENYL 1,3 DITHIOPHTHALIMIDE; HORMONE RECEPTOR BLOCKING AGENT; LIVER X RECEPTOR ALPHA; LIVER X RECEPTOR ANTAGONIST; LIVER X RECEPTOR BETA; N 2' BUTYLPHENYLPHTHALIMIDE; N 2' ETHYLPHENYLPHTHALIMIDE; N 2' HEXYLPHENYLPHTHALIMIDE; N 2' METHYLPHENYLPHTHALIMIDE; N 2' N PROPYLPHENYLPHTHALIMIDE; N 2' PENTYLPHENYL 2,3 DIHYDROISOINDOLE 1,3 DITHIONE; N 2' PENTYLPHENYL 3 THIOXO 2,3 DIHYDROISOINDOL 1 ONE; N 2' PENTYLPHENYLPHTHALIMIDE; THALIDOMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CONTROLLED STUDY; DRUG EFFECT; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

CELL LINE, TUMOR; DNA-BINDING PROTEINS; ENZYME INHIBITORS; GENES, REPORTER; GLUCOSIDASES; HUMANS; HYPNOTICS AND SEDATIVES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; PHTHALIMIDES; RECEPTORS, CYTOPLASMIC AND NUCLEAR; STRUCTURE-ACTIVITY RELATIONSHIP; THALIDOMIDE;

EID: 36849019370     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.1750     Document Type: Article

References (23)

1. Chawla A., Pepa J. J., Evans R., Mangelsdorf D. J., Science, 294, 1866-1870 (2001).
2. Janowski B. A., Willy P. J., Devi T. R., Falck J. R., Mangelsdorf D. J., Nature (London), 383, 728-731 (1996).
3. Lehmann J. M., Kliewer S. A., Moore L. B., Smith-Oliver T. A., Blanchard D. E., Spencer T. A., Willson T. M., J. Biol. Chem., 272, 3137-3140 (1997).
4. Collins J. L., Fivush A. M., Watson M. A., Galardi C. M., Lewis M. C., Moore L. B., Parks D. J., Wilson J. G., Tippin T. K., Binz J. G., Plunket K. D., Morgan D. G., Beaudet E. G., Whitney K. D., Kliewer S. A., Willson T. M., J. Med. Chem., 45, 1963-1966 (2002).
5. Schults J. R., Tu H., Luk A., Repa J. J., Medina J. C., Li L., Schwendner S., Wang S., Thoolen M., Mangelsdorf D. J., Lustig K. D., Shan B., Genes Develop., 14, 2831-2838 (2000).
6. Repa J. J., Turley S. D., Lobaccaro J. M. A., Medina J., Li L., Lustig K., Shan B., Heyman R. A., Dietschy J. M., Mangelsdorf D. J., Science, 289, 1524-1529 (2000).
7. Peet D. J., Turley S. D., Ma W., Janowski B. A., Lobaccaro J. M. A., Hammer R. E., Mangelsdorf D. J., Cell, 93, 693-704 (1998).
8. Laffitte B. A., Chao L. C., Li J., Walczak R., Hummasti S., Joseph S. B., Castrillo A., Wilpitz D. C., Mangelsdorf D. J., Collins J. L., Saez E., Tontonoz P., Proc. Natl. Acad. Sci. U.S.A., 100, 5419-5424 (2003).
9. Cao G., Liang Y., Broderick C. L., Oldham B. A., Beyer T. P., Schmidt R. J., Zhang Y., Stayrook K. R., Suen C., Otto K. A., Miller A. R., Dai J., Foxworthy P., Gao H., Ryan T. P., Jiang X. C., Burris T. P., Eacho P. I., Etgen G. J., J. Biol. Chem., 278, 1131-1136 (2003).
10. Mitro N., Mak P. A., Vatgas L., Godio C., Hampton E., Molteni V., Kreusch A., Saez E., Nature (London), 445, 219-223 (2007).
11. Hashimoto Y., Curr. Med. Chem., 5, 163-178 (1998).
12. Hashimoto Y., Bioorg. Med. Chem., 10, 461-479 (2002).
13. Hashimoto Y., Tanatani A., Nagasawa K., Miyachi H., Drugs Future, 29, 383-391 (2004).
14. Hashimoto Y., Mini-Rev. Med. Chem., 2, 543-551 (2002).
15. Shimazawa R., Takayama H., Fujimoto Y., Komoda M., Dodo K., Yamasaki R., Shirai R., Koiso Y., Miyata K., Kato F., Kato M., Miyachi H., Hashimoto Y., J. Enzyme Inhibit., 14, 249-275 (1999).
16. Sou S., Mayumi S., Takahashi H., Yamasaki R., Kadoya S., Sodeoka M., Hashimoto Y., Bioorg. Med. Chem. Lett., 10, 1081-1084 (2000).
17. Takahashi H,, Sou S., Yamasaki R., Sodeoka M., Hashimoto Y., Chem. Pharm. Bull., 48, 1494-1499 (2000).
18. Sou S., Takahashi H., Yamasaki R., Kagechika H., Endo Y., Hashimoto Y., Chem. Pharm. Bull., 49, 791-793 (2001).
19. Shimazawa R., Takayama H., Kato F., Kato M., Hashimoto Y., Bioorg. Med. Chem. Lett., 9, 559-562 (1999).
20. Noguchi-Yachide T., Aoyama A., Makishima M., Miyachi H., Hashimoto Y., Bioorg. Med. Chem. Lett., 17, 3957-3961 (2007).
21. Makishima M., Lu T. T., Xie W., Whitfield G. K., Domoto H., Evans R. M., Haussler M. R., Mangelsdorf D. J., Science, 296, 1313-1316 (2002).
22. Makishima M., Okamoto A. Y., Repa J. J., Tu H., Learned R. M., Luk A., Hull M. V., Lustig K. D., Mangelsdorf D. J., Shan B., Science, 284, 1362-1365 (1999).
23. Kasuga J., Makishima M., Hashimoto Y., Miyachi H., Bioorg. Med. Chem. Lett., 16, 554-558 (2006).