Novel phenoxyalkylcarboxylic acid derivatives as hypolipidaemic agents

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 2, 2012, Pages 311-318

  Li, Wei ^a,b   Jia, Hao Yan ^a   He, Xin Hua ^a   Shi, Wei Guo ^a   Zhong, Bo Hua ^a  

^a BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

^b INSTITUTE OF MICROBIOLOGY   (China)

Author keywords

Flavonoids; Hypolipidaemic; PPAR ; Resveratrol; Scaffolds

Indexed keywords

4' (1 METHYL 1 CARBOXYLETHOXY) 5,7 DIHYDROXYISOFLAVONE; 4' (1 METHYL 1 CARBOXYLETHOXY) 7 HYDROXYISOFLAVONE; 4' (1 METHYL 1 ETHOXYCARBOXYLETHOXY) 5 HYDROXY 7 METHOXYMETHOXYISOFLAVONE; 4' (1 METHYL 1 ETHOXYCARBOXYLETHOXY) 5,7 DIHYDROXYISOFLAVONE; 4' (1 METHYL 1 ETHOXYCARBOXYLETHOXY) 7 HYDROXYISOFLAVONE; 4' (1 METHYL 1 ETHOXYCARBOXYLETHOXY) 7 METHOXYMETHOXYISOFLAVONE; 4' HYDROXY 7 METHOXYMETHOXYISOFLAVONE; 4',5 DIHYDROXY 7 METHOXYMETHOXYISOFLAVONE; 5 HYDROXY 7 (1 METHYL 1 CARBOXYLETHOXY) FLAVONE; 5 HYDROXY 7 (1 METHYL 1 ETHOXYCARBOXYLETHOXY)FLAVONE; ANTILIPEMIC AGENT; CARBOXYLIC ACID DERIVATIVE; CHOLESTEROL; CHRYSIN; DAIDZEIN; FENOFIBRATE; FENOFIBRIC ACID; FORMONONETIN; GEMFIBROZIL; GENISTEIN; ISOLIQUIRITIGENIN; NARINGENIN; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PHENOXYALKYLCARBOXYLIC ACID DERIVATIVE; RESVERATROL; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ALLOXAN DIABETES MELLITUS; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOLOGICAL ACTIVITY; CHOLESTEROL BLOOD LEVEL; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; HYPERLIPIDEMIA; LIGAND BINDING; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; CARBOXYLIC ACIDS; CHOLESTEROL; DIABETES MELLITUS, EXPERIMENTAL; FENOFIBRATE; FLAVONOIDS; HYPERLIPIDEMIAS; HYPOLIPIDEMIC AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; STILBENES; SURFACE-ACTIVE AGENTS; TRIGLYCERIDES;

MUS;

EID: 84863240601     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.589840     Document Type: Article

References (39)

1. Anum EA, Adera T. Hypercholesterolemia and coronary heart disease in the elderly: a meta-analysis. Ann Epidemiol 2004;14:705-721. (Pubitemid 39233631)
2. Auboeuf D, Rieusset J, Fajas L, Vallier P, Frering V, Riou JP et al. Tissue distribution and quantifcation of the expression of mRNAs of peroxisome proliferator-activated receptors and liver X receptor-alpha in humans: no alteration in adipose tissue of obese and NIDDM patients. Diabetes 1997;46:1319-1327. (Pubitemid 27315281)
3. Banner CD, Göttlicher M, Widmark E, Sjövall J, Rafter JJ, Gustafsson JA. A systematic analytical chemistry/cell assay approach to isolate activators of orphan nuclear receptors from biological extracts: characterization of peroxisome proliferator-activated receptor activators in plasma. J Lipid Res 1993;34:1583-1591. (Pubitemid 23264331)
4. Chong PH, Bachenheimer BS. Current, new and future treatments in dyslipidaemia and atherosclerosis. Drugs 2000;60: 55-93. (Pubitemid 30598819)
5. Brown PJ, Winegar DA, Plunket KD, Moore LB, Lewis MC, Wilson JG et al. A ureido-thioisobutyric acid (GW9578) is a subtype-selective PPARalpha agonist with potent lipid-lowering activity. J Med Chem 1999;42:3785-3788. (Pubitemid 29453459)
6. Bunnelle WH, Dart MJ, Schrimpf MR. Design of ligands for the nicotinic acetylcholine receptors: the quest for selectivity. Curr Top Med Chem 2004;4:299-334. (Pubitemid 38849362)
7. Kersten S, Desvergne B, Wahli W. Roles of PPARs in health and disease. Nature 2000;405:421-424. (Pubitemid 30367411)
8. Willson TM, Brown PJ, Sternbach DD, Henke BR. Te PPARs: from orphan receptors to drug discovery. J Med Chem 2000;43:527-550. (Pubitemid 30127149)
9. Fruchart JC, Staels B, Duriez P. Te role of fbric acids in atherosclerosis. Curr Atheroscler Rep 2001;3:83-92.
10. Shek A, Ferrill MJ. Statin-fbrate combination therapy. Ann Pharmacother 2001;35:908-917.
11. Adverse Drug Reactions Advisory Committee. Risk factors for myopathy and rhabdomyolysis with the statins. Aust Adv Drug React Bull 2004;23:2.
12. Jones PH, Davidson MH. Reporting rate of rhabdomyolysis with fenofbrate + statin versus gemfbrozil + any statin. Am J Cardiol 2005;95:120-122. (Pubitemid 40051126)
13. Laboratoires Fournier SA. Lipidil (Fenofbrate) Product Information, 13 October 2003.
14. Peters JM, Cattley RC, Gonzalez FJ. Role of PPAR alpha in the mechanism of action of the nongenotoxic carcinogen and peroxisome proliferator Wy-14,643. Carcinogenesis 1997;18:2029-2033.
15. Staels B, Dallongeville J, Auwerx J, Schoonjans K, Leitersdorf E, Fruchart JC. Mechanism of action of fbrates on lipid and lipoprotein metabolism. Circulation 1998;98:2088-2093. (Pubitemid 28512236)
16. Jeremy PES. Flavonoids: modulators of brain function? Br J Nutr 2008;99:ES60-ES77.
17. Cushnie TP, Lamb AJ. Antimicrobial activity of favonoids. Int J Antimicrob Agents 2005;26:343-356.
18. "Studies force new view on biology of favonoids", by David Stauth, EurekAlert!. Adapted from a news release issued by Oregon State University. URL accessed.
19. Alan L, Miller ND. Antioxidant favonoids: structure, function and clinical usage. Altern Med Rev 1996;1:103-111.
20. Stivala LA, Savio M, Carafoli F, Perucca P, Bianchi L, Maga G et al. Specifc structural determinants are responsible for the antioxidant activity and the cell cycle efects of resveratrol. J Biol Chem 2001;276:22586-22594.
21. Kimura Y, Okuda H, Arichi S. Efects of stilbenes on arachidonate metabolism in leukocytes. Biochim Biophys Acta 1985;834:275-278. (Pubitemid 15072791)
22. Mannila E, Talvitie A, Kolehmainen E. Xanthone O-glycosides from Polygala tenuifolia. Phytochemistry 1993;33:813-816.
23. Mahady GB, Pendland SL, Chadwick LR. Resveratrol and red wine extracts inhibit the growth of CagA+ strains of Helicobacter pylori in vitro. Am J Gastroenterol 2003;98:1440-1441. (Pubitemid 36741550)
24. Creasy LL, Cofee M. Phytoalexin production potential of grape berries. J Am Soc Hortic Sci 1988;113:230-234.
25. Chung MI, Teng CM, Cheng KL, Ko FN, Lin CN. An antiplatelet principle of Veratrum formosanum. Planta Med 1992;58:274-276.
26. Inamori Y, Kubo M, Tsujibo H, Ogawa M, Saito Y, Miki Y et al. Te ichthyotoxicity and coronary vasodilator action of 3,3′-dihydroxy-alpha, beta-diethylstilbene. Chem Pharm Bull 1987;35: 887-890. (Pubitemid 17039981)
27. Schneider Y, Duranton B, Gossé F, Schleifer R, Seiler N, Raul F. Resveratrol inhibits intestinal tumorigenesis and modulates host-defense-related gene expression in an animal model of human familial adenomatous polyposis. Nutr Cancer 2001;39: 102-107. (Pubitemid 32880955)
28. Hegsted DM, Ausman LM. Diet, alcohol and coronary heart disease in men. J Nutr 1988;118:1184-1189.
29. Renaud S, de Lorgeril M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 1992;339:1523-1526.
30. Baur JA, Sinclair DA. Terapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov 2006;5:493-506. (Pubitemid 44136961)
31. Frankel EN, Waterhouse AL, Kinsella JE. Inhibition of human LDL oxidation by resveratrol. Lancet 1993;341:1103-1104. (Pubitemid 23114451)
32. Ungvari Z, Orosz Z, Rivera A, Labinskyy N, Xiangmin Z, Olson S et al. Resveratrol increases vascular oxidative stress resistance. Am J Physiol Heart Circ Physiol 2007;292:H2417-H2424. (Pubitemid 47084624)
33. Wang Z, Zou J, Huang Y, Cao K, Xu Y, Wu JM. Efect of resveratrol on platelet aggregation in vivo and in vitro. Chin Med J 2002;115:378-380.
34. Arichi H, Kimura Y, Okuda H, Baba K, Kozawa M, Arichi S. Efects of stilbene components of the roots of Polygonum cuspidatum Sieb. et Zucc. on lipid metabolism. Chem Pharm Bull 1982;30:1766-1770. (Pubitemid 12029652)
35. Rimando AM, Nagmani R, Feller DR, Yokoyama W. Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters. J Agric Food Chem 2005;53:3403-3407. (Pubitemid 40758174)
36. Li Z, Liao C, Ko BC, Shan S, Tong EH, Yin Z et al. Design, synthesis, and evaluation of a new class of noncyclic 1,3-dicarbonyl compounds as PPARalpha selective activators. Bioorg Med Chem Lett 2004;14:3507-3511. (Pubitemid 38737156)
37. Sierra ML, Beneton V, Boullay AB, Boyer T, Brewster AG, Donche F et al. Substituted 2-[(4-aminomethyl)phenoxy]-2-methylpropionic acid PPARalpha agonists. 1. Discovery of a novel series of potent HDLc raising agents. J Med Chem 2007;50:685-695. (Pubitemid 46332981)
38. Mizuno CS, Ma G, Khan S, Patny A, Avery MA, Rimando AM. Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARalpha. Bioorg Med Chem 2008;16:3800-3808. (Pubitemid 351484033)
39. Xu HE, Lambert MH, Montana VG, Plunket KD, Moore LB, Collins JL et al. Structural determinants of ligand binding selectivity between the peroxisome proliferator-activated receptors. Proc Natl Acad Sci usa 2001;98:13919-13924. (Pubitemid 33115999)