Indole-based fibrates as potential hypolipidemic and antiobesity agents

Journal of Medicinal Chemistry

Volumn 55, Issue 6, 2012, Pages 2769-2779

  Sashidhara, Koneni V ^a   Kumar, Manoj ^a   Sonkar, Ravi ^a   Singh, Bhanu Shankar ^b   Khanna, A K ^a   Bhatia, Gitika ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b National Institute of Pharmaceutical Education and Research (NIPER)   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTILIPEMIC AGENT; ANTIOBESITY AGENT; FIBRIC ACID DERIVATIVE; INDOLE; LOW DENSITY LIPOPROTEIN; PHOSPHATIDYLCHOLINE STEROL ACYLTRANSFERASE; TYLOXAPOL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CATABOLISM; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME BLOOD LEVEL; FEEDING BEHAVIOR; HISTOLOGY; HYPERLIPIDEMIA; INTRAABDOMINAL FAT; LIPID DIET; NONHUMAN; RAT; WEIGHT REDUCTION;

ANIMALS; ANTI-OBESITY AGENTS; BILE ACIDS AND SALTS; BUTYRATES; DIETARY FATS; FATTY LIVER; FECES; FEEDING BEHAVIOR; FIBRIC ACIDS; HYPERLIPIDEMIAS; HYPOLIPIDEMIC AGENTS; INDOLES; INTRA-ABDOMINAL FAT; LIPOPROTEINS, LDL; LIVER; MALE; PHOSPHATIDYLCHOLINE-STEROL O-ACYLTRANSFERASE; PROPIONATES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; WEIGHT LOSS;

EID: 84858727175     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201697v     Document Type: Article

References (48)

1. Wickelgren, I. Obesity: How Big a Problem? Science 1998, 280, 1364-1367 (Pubitemid 28264814)
2. Bray, G. A. Obesity: the disease J. Med. Chem. 2006, 49, 4001-4007 (Pubitemid 44036645)
3. Flegal, K. M.; Carroll, M. D.; Ogden, C. L.; Johnson, C. L. Prevalence and trends in obesity among US adults, 1999-2000 JAMA 2002, 288, 1723-1727
4. The World Health Report 2002: Reducing Risks, Promoting a Healthy Life; World Health Organization: Geneva, Switzerland, 2002.
5. Jong, W. Y. Possible anti-Obesity drugs from nature- a review Phytochemistry 2010, 71, 1625-1641
6. Drew, B. S.; Dixon, A. F.; Dixon, J. B. Obesity management: update on orlistat Vasc. Health Risk Manag. 2007, 3, 817-821
7. Tziomalos, K.; Krassas, G. E.; Tzotzas, T. The use of sibutramine in the management of obesity and related disorders: an update Vasc. Health Risk Manag. 2009, 5, 441-452
8. De Simone, G.; D'Addeo, G. Sibutramine: balancing weight loss benefit and possible cardiovascular risk Nutr. Metab. Cardiovasc. Dis. 2008, 18, 337-341
9. Slovacek, L.; Pavlik, V.; Slovackova, B. The effect of sibutramine therapy on occurrence of depression symptoms among obese patients Nutr. Metab. Cardiovasc. Dis. 2008, 18, e43-e44
10. Karamadoukis, L.; Shivashankar, G. H.; Ludeman, L.; Williams, A. J. An unusual complication of treatment with orlistat Clin. Nephrol. 2009, 71, 430-432
11. Agulera, C. M.; Gil-Compos, M.; Canete, R.; Gil, A. Alterations in plasma and tissue lipids associated with obesity and metabolic syndrome Clin. Sci. 2008, 114, 183-193 (Pubitemid 351293994)
12. Lalloyer, F.; Staels, B. Fibrates, glitazones, and peroxisome proliferator-activated receptors Arterioscler., Thromb., Vasc. Biol. 2010, 30, 894-899
13. Davidson, M. H.; Armani, A.; McKenney, J. M.; Jacobson, T. A. Safety considerations with fibrate therapy Am. J. Cardiol. 2007, 99, 3C-18C
14. Barker, B. J.; Goodenough, R. R.; Falko, J. M. Fenofibrate monotherapy induced rhabdomyolysis Diabetes Care 2003, 26, 2482-2483
15. Shek, A.; Ferrill, M. J. Statin-fibrate combination therapy Ann. Pharmacother. 2001, 35, 908-917 (Pubitemid 32678717)
16. Sashidhara, K. V.; Kumar, A.; Kumar, M.; Sarkar, J.; Sinha, S. Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents Bioorg. Med. Chem. Lett. 2010, 20, 7205-7211
17. Sashidhara, K. V.; Kumar, M.; Modukuri, R. K.; Sonkar, R.; Khanna, A. K.; Bhatia, G.; Rai, S.; Shukla, R. Synthesis and anti-inflammatory activity of novel biscoumarin-chalcone hybrids Bioorg. Med. Chem. Lett. 2011, 21, 4480-4484
18. Sashidhara, K. V.; Kumar, A.; Kumar, M.; Singh, S.; Jain, M.; Dikshit, M. Synthesis of novel 3-carboxamide-benzocoumarin derivatives as orally active antithrombotic agents Bioorg. Med. Chem. Lett. 2011, 21, 7034-7040
19. Sashidhara, K. V.; Kumar, A.; Kumar, M.; Srivastava, A.; Puri, A. Synthesis and antihyperlipidemic activity of novel coumarin bisindole derivatives Bioorg. Med. Chem. Lett. 2010, 20, 6504-6507
20. Velezheva, V. S.; Brennan, P. J.; Marshakov, V. Y.; Gusev, D. V.; Lisichkina, I. N.; Peregudov, A. S.; Tchernousova, L. N.; Smirnova, T. G.; Andreevskaya, S. N.; Medvedev, A. E. Novel pyridazino[4,3-b]indoles with dual inhibitory activity against Mycobacterium tuberculosis and monoamine oxidase J. Med. Chem. 2004, 47, 3455-3461 (Pubitemid 38746096)
21. Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Landi, L.; Prata, C.; Berridge, M. V.; Grasso, C.; Fiebig, H. H.; Kelter, G.; Burger, A. M.; Kunkel, M. W. Antitumor activity of bis-indole derivatives J. Med. Chem. 2008, 51, 4563-4570
22. Routier, S.; Peixoto, P.; Mérour, J. Y.; Coudert, G.; Dias, N.; Pierré, C. B. A.; Léonce, S.; Caignard, D. H. Synthesis and biological evaluation of novel naphthocarbazoles as potential anticancer agents J. Med. Chem. 2005, 48, 1401-1413 (Pubitemid 40372209)
23. Regina, G. L.; Coluccia, A.; Piscitelli, F.; Bergamini, A.; Sinistro, A.; Cavazza, A.; Maga, G.; Samuele, A.; Zanoli, S.; Novellino, E.; Artico, M.; Silvestri, R. Indolyl aryl sulfones as HIV-1 non-nucleoside reverse transcriptase inhibitors: role of two halogen atoms at the indole ring in developing new analogues with improved antiviral activity J. Med. Chem. 2007, 50, 5034-5038 (Pubitemid 47525483)
24. Knott, K. E.; Auschill, S.; Jäger, A.; Knölker, H. J. First total synthesis of the whole series of the antiostatins A and B Chem. Commun. 2009, 12, 1467-1469
25. Cowley, P. M.; Baker, J.; Barn, D. R.; Buchanan, K. I.; Carlyle, I.; Clark, J. K.; Clarkson, T. R.; Deehan, M.; Edwards, D.; Goodwin, R. R.; Jaap, D.; Kiyoi, Y.; Mort, C.; Palin, R.; Prosser, A.; Walker, G.; Ward, N.; Wishart, G.; Young, T. The discovery of novel indole-2-carboxamides as cannabinoid CB1 receptor antagonists Bioorg. Med. Chem. Lett. 2011, 21, 497-501
26. Morrison, A. J.; Adam, J. M.; Baker, J. A.; Campbell, R. A.; Clark, J. K.; Cottney, J. E.; Deehan, M.; Easson, A. M.; Fields, R.; Francis, S.; Jeremiah, F.; Keddie, N.; Kiyoi, T.; McArthur, D. R.; Meyer, K.; Ratcliffe, P. D.; Schulz, J.; Wishart, G.; Yoshiizumi, K. Design, synthesis, and structure-activity relationships of indole-3-heterocycles as agonists of CB1 receptor Bioorg. Med. Chem. Lett. 2011, 21, 506-509
27. Pierson, P. D.; Fettes, A.; Freichel, C.; Gatti-McArthur, S.; Hertel, C.; Huwyler, J.; Mohr, P.; Nakagawa, T.; Nettekoven, M.; Plancher, J. M.; Raab, S.; Richter, H.; Roche, O.; Sarmiento, R. M. R.; Schmitt, M.; Schuler, F.; Takahashi, T.; Taylor, S.; Ullmer, C.; Wiegand, R. 5-Hydroxyindole-2-carboxylic acid amides: Novel histamine-3 receptor inverse agonists for the treatment of obesity J. Med. Chem. 2009, 52, 3855-3868
28. Sashidhara, K. V.; Kumar, A.; Bhatia, G.; Khan, M. M.; Khanna, A. K.; Saxena, J. K. Antidyslipidemic and antioxidative activities of 8-hydroxyquinoline derived keto-enamine schiffs bases Eur. J. Med. Chem. 2009, 44, 1813-1818
29. Howard, B. V.; Ruotolo, G.; Robbins, D. C. Obesity and dyslipidemia Endocrinol. Metab. Clin. North Am. 2003, 32, 855-867 (Pubitemid 38029984)
30. Colca, J. R.; Dailey, C. F.; Palazuk, B. J.; Hillman, R. M.; Dinh, D. M.; Melchior, G. W.; Spilman, C. H. Pioglitazone hydrochloride inhibits cholesterol absorption and lowers plasma cholesterol concentrations in cholesterol-fed rats Diabetes 1991, 40, 1669-1674
31. Rijzewijk, L. J.; Van der Meer, R. W.; Lubberink, M.; Lamb, H. J.; Romijn, J. A.; Roos, A.; Twisk, J. W.; Heine, R. J.; Lammertsma, A. A.; Smit, J. W.; Diamant, M. Liver fat content in type 2 diabetes: relationship with hepatic perfusion and substrate metabolism Diabetes 2010, 59, 2747-2754
32. Bhuiyan, M. J.; Do, H. V.; Mun, S.; Jun, H. J.; Lee, J. H.; Kim, Y. R.; Lee, S. J. Hypocholesterolemic and hypoglycemic effects of enzymatically modified carbohydrates from rice in high-fat-fed C57BL/6J mice Mol. Nutr. Food Res. 2011, 55, S214-S226
33. Lees, R. Hyperlipidemia and Atherosclerosis HST.151: Principles of Pharmacology; http://ocw.mit.edu/courses (Accessed on October 16, 2011).
34. Windler, E. E.; Kovanen, P. T.; Chao, Y. S.; Brown, M. S.; Havel, R. J. The estradiol-stimulated lipoprotein receptor of rat liver. A binding site that membrane mediates the uptake of rat lipoproteins containing apoproteins B and E J. Biol. Chem. 1980, 255, 10464-10471 (Pubitemid 11219979)
35. Anstee, Q. M.; Goldin, R. D. Mouse models in non-alcoholic fatty liver disease and steatohepatitis research Int. J. Exp. Pathol. 2006, 87, 1-16
36. Rahman, S. M.; Wang, Y.; Yotsumoto, H.; Cha, J.; Han, S.; Inoue, S.; Yanagita, T. Effects of conjugated linoleic acid on serum leptin concentration, body-fat accumulation, and beta-oxidation of fatty acid in OLETF rats Nutrition 2001, 17, 385-390 (Pubitemid 32457803)
37. Reddy, J. K.; Rao, M. S. Lipid metabolism and liver inflammation. II. Fatty liver disease and fatty acid oxidation Am. J. Physiol. Gastrointest. Liver Physiol. 2006, 290, G852-G858
38. Jeon, J. R.; Kim, J. Y. Effects of pine needle extract on differentiation of 3T3-L1 preadipocytes and obesity in high-fat diet fed rats Biol. Pharm. Bull. 2006, 29, 2111-2115
39. 2O/TTBP (2,4,6-tri-tert-butylpyridine) system Org. Lett. 2011, 13, 4854-4857
40. Seefeld, M. A.; Miller, W. H.; Newlander, K. A.; Burgess, W. J.; Dewolf, W. E., Jr.; Elkins, P. A.; Head, M. S.; Jakas, D. R.; Janson, C. A.; Keller, P. M.; Manley, P. J.; Rittenhouse, S. F.; Uzinskas, I. N.; Wallis, N. G.; Huffman, W. F. Indole naphthyridinones as inhibitors of bacterial enoyl-ACP reductases FabI and FabK J. Med. Chem. 2003, 46, 1627-1635 (Pubitemid 36444216)
41. Bhaumik, J.; Yao, Z.; Borbas, K. E.; Taniguchi, M.; Lindsey, J. S. Masked imidazoyl-dipyrromethanes in the synthesis of imidazole-substituted porphyrins J. Org. Chem. 2006, 71, 8807-8817 (Pubitemid 44721953)
42. Sierra, M. L.; Beneton, V.; Boullay, A. N.; Boyer, T.; Brewster, A. G.; Donche, F.; Forest, M. C.; Fouchet, M. H.; Gillibert, F. J.; Grillot, D. A.; Lambert, M. H.; Laroze, A.; Grumelec, C. L.; Linget, J. M.; Montana, V. G.; Nguyen, V. L.; Nicodeme, E.; Patel, V.; Penfornis, A.; Pineau, O.; Pohin, D.; Potvain, F.; Paulain, G.; Ruault, C. B.; Saunders, M.; Taum, J.; Xu, H. E.; Xu, R. X.; Pianetti, P. M. Substituted 2-[(4-Aminomethyl)phenoxy]-2-methylpropionic acid PPARα agonists. 1. Discovery of a novel series of potent HDLc raising agents J. Med. Chem. 2007, 50, 685-695 (Pubitemid 46332981)
43. Fraga-Dubreuil, J.; Bazureau, J. P. Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to one-pot three component synthesis of a small library of 4-thiazolidinones Tetrahedron 2003, 59, 6121-6130 (Pubitemid 36897766)
44. Khanna, A. K.; Chander, R.; Singh, C.; Srivastava, A. K.; Kapoor, N. K. Hypolipidemic activity of Terminalia chebula in rats Fitoterpia 1993, 64, 351-356 (Pubitemid 23303649)
45. Wing, D. R.; Robinson, D. S. Clearing-factor lipase in adipose tissue. A possible role of adenosine 3′,5′-(cyclic)-monophosphate in the regulation of its activity Biochem. J. 1968, 109, 841-849
46. Kovanen, P. T.; Brown, M. S.; Goldstein, J. L. Increased binding of low density lipoprotein to liver membranes from rats treated with 17 alpha-ethinyl estradiol J. Biol. Chem. 1979, 254, 11367-11373 (Pubitemid 10136151)
47. Singh, V.; Kaul, S.; Chander, R.; Kapoor, N. K. Stimulation of low density lipoprotein receptor activity in liver membrane of guggulsterone treated rats Pharmacol. Res. 1990, 22, 37-44 (Pubitemid 20139438)
48. Mosbach, E. H.; Klenisky, H. J.; Hal, P.; Kendall, F. E. Determination of deoxycholic acid cholic acid in bile Arch. Biochem. Biophys. 1954, 51, 402-409