Synthesis and evaluation of diarylthiazole derivatives that inhibit activation of sterol regulatory element-binding proteins

Journal of Medicinal Chemistry

Volumn 54, Issue 13, 2011, Pages 4923-4927

  Kamisuki, Shinji ^a   Shirakawa, Takashi ^a   Kugimiya, Akira ^a   Abu Elheiga, Lutfi ^b   Park Choo, Hea Young ^a,c   Yamada, Kohei ^a   Shimogawa, Hiroki ^a   Wakil, Salih J ^b   Uesugi, Motonari ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b BAYLOR COLLEGE OF MEDICINE   (United States)

^c Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

4 (2 METHOXYPHENYL) 2 (2 PROPYLPYRIDIN 4 YL)THIAZOLE; FATOSTATIN DERIVATIVE; FGH 10019; N [4 [2 (2 PROPYLPYRIDIN 4 YL)THIAZOL 4 YL]PHENYL]METHANESULFONAMIDE; N ISOPROPYL 4 [2 (2 PROPYLPYRIDIN 4 YL)THIAZOL 4 YL]ANILINE; STEROL REGULATORY ELEMENT BINDING PROTEIN; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; WARFARIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BODY WEIGHT; CONTROLLED STUDY; DRUG CLEARANCE; DRUG HALF LIFE; DRUG INHIBITION; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; FOOD INTAKE; IC 50; LIVER CELL; MALE; MEMBRANE PERMEABILITY; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; PROTEIN EXPRESSION; REPORTER GENE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; BLOOD GLUCOSE; CHO CELLS; CRICETINAE; CRICETULUS; EATING; HEPATOCYTES; MALE; MEMBRANES, ARTIFICIAL; MICE; MICE, OBESE; PERMEABILITY; PYRIDINES; SOLUBILITY; STEROL REGULATORY ELEMENT BINDING PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIAZOLES;

EID: 79960181626     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200304y     Document Type: Article

References (14)

1. Brown, M. S.; Goldstein, J. L. The SREBP pathway: regulation of cholesterol metabolism by proteolysis of a membrane-bound transcription factor Cell 1997, 89, 331-340 (Pubitemid 27220877)
2. Osborne, T. F. Sterol regulatory element-binding proteins (SREBPs): key regulators of nutritional homeostasis and insulin action J. Biol. Chem. 2000, 275, 32379-32382
3. Sakai, J.; Duncan, E. A.; Rawson, R. B.; Hua, X.; Brown, M. S.; Goldstein, J. L. Sterol-regulated release of SREBP-2 from cell membranes requires two sequential cleavages, one within a transmembrane segment Cell 1996, 85, 1037-1046 (Pubitemid 26231170)
4. Goldstein, J. L.; DeBose-Boyd, R. A.; Brown, M. S. Protein sensors for membrane sterols Cell 2006, 124, 35-46
5. Hua, X.; Nohturfft, A.; Goldstein, J. L.; Brown, M. S. Sterol resistance in CHO cells traced to point mutation in SREBP cleavage-activating protein Cell 1996, 87, 415-426 (Pubitemid 26374316)
6. Radhakrishnan, A.; Sun, L. P.; Kwon, H. J.; Brown, M. S.; Goldstein, J. L. Direct binding of cholesterol to the purified membrane region of SCAP: mechanism for a sterol-sensing domain Mol. Cell 2004, 15, 259-268 (Pubitemid 38950972)
7. Yang, T.; Espenshade, P. J.; Wright, M. E.; Yabe, D.; Gong, Y.; Aebersold, R.; Goldstein, J. L.; Brown, M. S. Crucial step in cholesterol homeostasis: sterols promote binding of SCAP to INSIG-1, a membrane protein that facilitates retention of SREBPs in ER Cell 2002, 110, 489-500 (Pubitemid 35232292)
8. Choi, Y.; Kawazoe, Y.; Murakami, K.; Misawa, H.; Uesugi, M. Identification of bioactive molecules by adipogenesis profiling of organic compounds J. Biol. Chem. 2003, 278, 7320-7324 (Pubitemid 36800734)
9. Kamisuki, S.; Mao, Q.; Abu-Elheiga, L.; Gu, Z.; Kugimiya, A.; Kwon, Y.; Shinohara, T.; Kawazoe, Y.; Sato, S.; Asakura, K.; Choo, H. Y.; Sakai, J.; Wakil, S. J.; Uesugi, M. A small molecule that blocks fat synthesis by inhibiting the activation of SREBP Chem. Biol. 2009, 16, 882-892
10. Comins, D. L.; Mantlo, N. B. Regiospecific alpha-alkylation of 4-chloro(bromo)pyridine J. Org. Chem. 1985, 50, 4410-4411
11. Bilgin, A. A. 2-Pyridylthiazoles II, synthesis and structure elucidations Acta Pharm. Turcica 1988, 30, 133-138
12. Adams, C. M.; Reitz, J.; De Brabander, J. K.; Feramisco, J. D.; Li, L.; Brown, M. S.; Goldstein, J. L. Cholesterol and 25-hydroxycholesterol inhibit activation of SREBPs by different mechanisms, both involving SCAP and Insigs J. Biol. Chem. 2004, 279, 52772-52780 (Pubitemid 39656653)
13. Horton, J. D.; Shah, N. A.; Warrington, J. A.; Anderson, N. N.; Park, S. W.; Brown, M. S.; Goldstein, J. L. Combined analysis of oligonucleotide microarray data from transgenic and knockout mice identifies direct SREBP target genes Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 12027-12032 (Pubitemid 37271509)
14. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25 (Pubitemid 27046991)