Discovery of a novel acyl-CoA: Cholesterol acyltransferase inhibitor: The synthesis, biological evaluation, and reduced adrenal toxicity of (4-phenylcoumarin)acetanilide derivatives with a carboxylic acid moiety

Chemical and Pharmaceutical Bulletin

Volumn 59, Issue 11, 2011, Pages 1369-1375

  Ogino, Masaki ^a   Nakada, Yoshihisa ^a   Negoro, Nobuyuki ^a   Itokawa, Shigekazu ^a   Nishimura, Satoshi ^a   Sanada, Tsukasa ^a   Satomi, Tomoko ^a   Kita, Shunbun ^a   Kubo, Kazuki ^a   Marui, Shogo ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

(4 phenylcoumarin)acetanilide; Acyl CoA: Cholesterol acyltransferase inhibitor; Adrenal toxicity; Atherosclerosis; Cholesterol; Macrophage

Indexed keywords

(4 PHENYLCOUMARIN)ACETANILIDE DERIVATIVE; 3 [7 CHLORO 3 [2 [[4 CHLORO 2 (TRIFLUOROMETHYL)PHENYL]AMINO] 2 OXOETHYL]] 6 METHYL 2 OXO 2H CHROMEN 4 YL]BENZOIC ACID; 3 [7 CHLORO 3 [2 [[4 FLUORO 2 (TRIFLUOROMETHYL)PHENYL]AMINO] 2 OXOETHYL] 6 METHYL 2 OXO 2H CHROMEN 4 YL]PHENYL]ACRYLIC ACID; CARBOXYLIC ACID; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ADRENAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; ATHEROSCLEROSIS; EXPERIMENTAL RABBIT; GUINEA PIG; HUMAN; HUMAN CELL; LIPOPHILICITY; MACROPHAGE; MALE; NONHUMAN;

ACETANILIDES; ACYL COENZYME A; ADMINISTRATION, ORAL; ADRENAL CORTEX; ANIMALS; ANTICHOLESTEREMIC AGENTS; CARBOXYLIC ACIDS; CELL LINE; COUMARINS; ENZYME INHIBITORS; GUINEA PIGS; HUMANS; MODELS, ANIMAL; RABBITS; STEROL O-ACYLTRANSFERASE;

EID: 81455155750     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.59.1369     Document Type: Article

References (17)

1. Libby P., J. Intern. Med., 263, 517-527 (2008).
2. Lee O., Chang C. C., Lee W., Chang T. Y., J. Lipid Res., 39, 1722-1727 (1998).
3. Buhman K. F., Accad M., Farese R. V., Biochim. Biophys. Acta, 1529, 142-154 (2000).
4. Rudel L. L., Lee R. G., Cockman T. L., Curr. Opin. Lipidol., 12, 121-127 (2001).
5. Chang T. Y., Li B. L., Chang C. C., Urano Y., Am. J. Physiol. Endocrinol. Metab., 297, E1-E9 (2009).
6. Chang T. Y., Chang C. C., Lin S., Yu C., Li B. L., Miyazaki A., Curr. Opin. Lipidol., 12, 289-296 (2001).
7. Oelkers P., Behari A., Cromley D., Billheimer J. T., Sturley S. L., J. Biol. Chem., 273, 26765-26771 (1998).
8. Miyazaki A., Kanome T., Watanabe T., Curr. Drug Targets Cardiovasc. Haematol. Disord., 5, 463-469 (2005).
9. Ikenoya M., Yoshinaka Y., Kobayashi H., Kawamine K., Shibuya K., Sato F., Sawanobori K., Watanabe T., Miyazaki A., Atherosclerosis, 191, 290-297 (2007).
10. Bocan T. M., Krause B. R., Rosebury W. S., Mueller S. B., Lu X., Dagle C., Major T., Lathia C., Lee H., Arterioscler. Thromb. Vasc. Biol., 20, 70-79 (2000).
11. Delsing D. J., Offerman E. H., van Duyvenvoorde W., van Der Boom H., de Wit E. C., Gijbels M. J., van Der Laarse A., Jukema J. W., Havekes L. M., Princen H. M., Circulation, 103, 1778-1786 (2001).
12. Ogino M., Fukui S., Nakada Y., Tokunoh R., Itokawa S., Kakoi Y., Nishimura S., Sanada T., Fuse H., Kubo K., Wada T., Marui S., Chem. Pharm. Bull., 59, 1268-1273 (2011).
13. Junquero D., Pilon A., Carilla-Durand E., Patoiseau J. F., Tarayre J. P., Torpier G., Staels B., Fruchart J. C., Colpaert F. C., Clavey V., Delhon A., Biochem. Pharmacol., 61, 387-398 (2001).
14. Sliskovic D. R., Picard J. A., O'Brien P. M., Liao P., Roark W. H., Roth B. D., Anderson M. A., Mueller S. B., Bocan T. M., Bousley R. F., Hamelehle K. L., Homan R., Reindel J. F., Stanfield R. L., Turluck D., Krause B. R., J. Med. Chem., 41, 682-690 (1998).
15. Robertson D. G., Breider M. A., Milad M. A., Toxicol. Sci., 59, 324-334 (2001).
16. Takahashi K., Kasai M., Ohta M., Shoji Y., Kunishiro K., Kanda M., Kurahashi K., Shirahase H., J. Med. Chem., 51, 4823-4833 (2008).
17. Chatterjea J. N., Jha H. C., Chattopadhyaya A. K., Justus Liebigs Ann. Chem., 1126-1131 (1974).