Novel indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives. Structure-activity relationships for high inhibition of human LDL peroxidation

Journal of Medicinal Chemistry

Volumn 40, Issue 8, 1997, Pages 1201-1210

  Kuehm Caubere, Catherine ^a   Caubere, Paul ^a   Jamart Gregoire, Brigitte ^a   Negre Salvayre, Anne ^c   Bonnefont Rousselot, Dominique ^d   Bizot Espiard, Jean Guy ^e   Pfeiffer, Bruno ^b   Caignard, Daniel Henri ^b   Guardiola Lemaitre, Béatrice ^e   Renard, Pierre ^b  

^a Biopôle de l Université de Lorraine   (France)

^b ADIR   (France)

^c UNIVERSITÉ DE TOULOUSE   (France)

^d PITIÉ SALPÊTRIÈRE HOSPITAL   (France)

^e INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[[BIS(4 FLUOROPHENYL)METHYL]PIPERAZINO]CARBONYL] 5 (HYDROXYMETHYL)INDOLE; 2 HYDROXY 5 METHYL 5,6,7,8,9,10 HEXAHYDROCYCLOHEPT[B]INDOLE; 2 INDOLECARBOXYLIC ACID; ALPHA TOCOPHEROL; ARACHIDONATE 5 LIPOXYGENASE; INDOLE DERIVATIVE; LOW DENSITY LIPOPROTEIN; PROBUCOL; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; ATHEROSCLEROSIS; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOTHELIUM CELL; INFLAMMATION; LIPID PEROXIDATION; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; CALCIMYCIN; COPPER; CYCLOPARAFFINS; DINOPROSTONE; GLYCINE AGENTS; HUMANS; INDOLES; IONOPHORES; LEUKOTRIENE B4; LIPID PEROXIDATION; LIPOPROTEINS, LDL; RABBITS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15144344775     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960542k     Document Type: Article

References (45)

1. Halliwel, B. Free radicals, relative oxygen species and human disease. Br. J. Exp. Pathol. 1989, 70, 737-757.
2. Braughler, J. M.; Hall, E. D. Central nervous system, trauma and stroke. I - Biochemical considerations for oxygen radical formation and lipid peroxidation. Free Rad. Biol. Med. 1989, 6, 289-301. II - Physiological and pharmacological evidence for involvement of oxygen radicals and lipid peroxidation. Free Rad. Biol. Med. 1989, 6, 303-313.
3. Braughler, J. M.; Hall, E. D. Central nervous system, trauma and stroke. I - Biochemical considerations for oxygen radical formation and lipid peroxidation. Free Rad. Biol. Med. 1989, 6, 289-301. II - Physiological and pharmacological evidence for involvement of oxygen radicals and lipid peroxidation. Free Rad. Biol. Med. 1989, 6, 303-313.
4. Panetta, J. A.; Clemens, J. A. Novel antioxidant therapy for cerebral ischemia-reperfusion injury. Ann. N.Y. Acad. Sci. 1994, 723, 239-245.
5. Bolli, R. Oxygen - derived free radical and myocardial reperfusion injury: an overview. Cardiovasc. Drugs Ther. 1991, 5, 249-268.
6. Werns, S. W.; Lucchesi, B. R. Free radicals and ischemic tissue injury. Trends Pharmacol. Sci. 1990, 11, 161-166.
7. Piotrowski, J. J.; Hunter, G. C.; Eskelson, C. D.; Dubick, M. A.; Bernhard, V. M. Evidence for lipid peroxidation in atherosclerosis. Life Sci. 1990, 46, 715-721.
8. Rubanyi, G. M. Vascular effects of oxygen - derived free radicals. Free Rad. Biol. Med. 1988, 4, 107-120.
9. Ross, R. The pathogenesis of atherosclerosis: a perspective for the 1990s. Nature 1993, 362, 801-809.
10. Hennig, B.; Cho, C. K. Lipid peroxidation and endothelial cell injury: implication in atherosclerosis. Free Rad. Biol. Med. 1988, 4, 99-106.
11. Esterbauer, H. Cytotoxicity and genotoxicity of lipid oxidation products. Am. J. Clin. Nutr. 1993, 57 (suppl), 7795-7865.
12. Yla-Herttuala, S.; Palinski, W.; Rosenfeld, M. E.; Parthasarathy, S.; Carew, T. E.; Butler, S.; Witztum, J. J.; Steinberg, D. Evidence for the presence of oxidatively modified low-density lipoprotein in atherosclerotic lesions of rabbit and man. J. Clin. Invest. 1989, 84, 1086-1095.
13. Steinberg, D.; Parthasarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 1989, 915-924.
14. Aviram, M. Modified forms of low-density lipoprotein and therosclerosis. Atherosclerosis 1993, 98, 1-9.
15. Reid, V. C.; Mitchinson, M. J. Toxicity of oxidised low-density lipoprotein toward mouse peritoneal macrophages in vitro. Atherosclerosis 1993, 98, 17-24.
16. Hodis, H. N.; Kramsch, D. M.; Avogaro, P.; Bittolo-Bon, G.; Cazzolato, G.; Hwang, J.; Peterson, H.; Sevanian, A. Biochemical and cytotoxic characteristics of an in vivo circulating oxidized low-density lipoprotein (LDL). J. Lipid Res. 1994, 35, 669-677.
17. Parthasarathy, S.; Rankin, S. M. Role of oxidized low-density lipoprotein in atherogenesis. Prog. Lipid Res. 1992, 31, 127-143.
18. Esterbauer, H.; Dieber-Rotheneder, M.; Waeg, G.; Striegl, G.; Jurgens, G. Biochemical structural and functional properties of oxidized low-density lipoprotein. Chem. Res. Toxicol. 1990, 3, 77-92.
19. Steinbrecher, U. P.; Zhang, H.; Lougheed, M. Role of oxidatively modified LDL in atherosclerosis. Free Rad. Biol. Med. 1988, 9, 155-168.
20. Witztum, J. L.; Steinberg, D. Role of oxidized low-density lipoprotein in atherogenesis. J. Clin. Invest. 1991, 88, 1785-1792.
21. Steinberg, D. Antioxidants in the prevention of human atherosclerosis. Summary of the proceedings of a national heart, lung and blood institute workshop: September 5-6, 1991, Bethesda, Maryland. Circulation 1992, 85, 2338-2344.
22. Dieber-Rotheneder, M.; Puhl, H.; Waeg, G.; Striegl, G.; Esterbauer, H. Effect of oral supplementation with D-α-tocopherol on the vitamin E content of human low-density lipoprotein and resistance to oxidation. J. Lipid Res. 1991, 32, 1325-1332.
23. Zimetbaumm, P.; Eder, H.; Frishman, W. Probucol: pharmacology and clinical application. J. Clin. Pharmacol. 1990, 30, 3-9.
24. Daugherty, A.; Zweifel, B. S.; Schonfeld, G. The effect of Probucol on the progression of atherosclerosis in mature Watanabe heritable hyperlipidaemic rabbits. Br. J. Pharmacol. 1991, 103, 1013-1018.
25. Mao, S. J. T.; Yates, M. T.; Rechtin, A. E.; Jackson, R. L.; Van Sickle, W. A. Antixoxidant activity of Probucol and its analogues in hypercholesterolemic Watanabe rabbits. J. Med. Chem. 1991, 34, 298-302.
26. Scott, J. W.; Cort, W. M.; Harley, H.; Parrish, D. R.; Saucy, G. 6-Hydroxychroman-2-carboxylic acids: novel antioxidants. J. Am. Oil Chem. Soc. 1994, 51, 200-203.
27. Jon Jacobsen, E.; Van Doornik, P. J.; Ayer, D. E.; Belonga, R. L.; Braughler, J. M.; Hall, E. D.; Houser, D. J. 2-(Aminomethyl) chromans that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma and ischemia. J. Med. Chem. 1992, 35, 4464-4472.
28. Linserman, D. A.; Wall, T. M.; Hartman. The Trolox analog, U-78517 F attenuates hyposcic injury in isolated cardiac myocyts. J. Mol. Cell Cardiol. 1994, 26, 1249-1257.
29. Yu, M. J.; McCowan, J. R.; Phebus, L. A.; Towner, R. D.; Ho, P. P. K.; Keith, P. T.; Luttman, C. A.; Saunders, R. D.; Ruterbories, K. J.; Lindstrom, T. D.; Wikel, J. H.; Morgan, E.; Hahn, R. A. Benzylamine antioxidant: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition, and cytoprotection. J. Med. Chem. 1993, 36, 1262-1271.
30. Cadenas, E.; Simic, M. G.; Sies, H. Antioxidant activity of 5-hydroxytryptophan, 5-hydroxyindole and DOPA against microsomal lipid peroxidation and its dependence on vitamin E. Free Rad. Res. Commun. 1989, 6, 11-17.
31. Halliwel, B.; Gutteridge, J. M. C., Lipid peroxydation: a radical chain reaction. In Free Radicals in Biology and Medecine; Oxford Science Publications: Oxford, 1985; pp 139-189.
32. Caubere, C.; Caubère, P.; Ianelli, S.; Nardelli, M.; Jamart-Grégoire, B. Aggregative activation and heterocyclic chemistry I. Complex Bases promoted arynic cyclisation of imines or enamino-ketones; Regiochemical synthesis of indoles. Tetrahedron 1994, 50 (41), 11903-11920.
33. Caubère, C.; Caubère, P.; Renard, P.; Bizot-Espiart, J. G.; Ianelli, S.; Nardelli, M.; Jamart-Grégoire, B. Functionalization of the Alkoxy group of Alkyl Aryl Ethers. Demethylation, Alkylthiolation and Reduction of 5-Methoxyindoles. Tetrahedron 1994, 50 (47), 13433-13448.
34. Ford-Hutchinson, A. W. Arachidonate 15-lipoxygenase; characteristics and potential biological significance. Eicosanoid 1991, 4, 65-74.
35. Graeber, J. E.; Glaser, B. M.; Setty, B. N. Y.; Jerdan, J. A.; Walenga, R. W.; Stuart, M. J. 15-Hydroxyeicosatetraenoic acid stimulated migration of human retinal microvessel endothelium in vitro and neovascularization in vivo. Prostaglandins 1990, 39, 665-673.
36. Parthasarathy, S.; Wieland, E.; Steinberg, D. A role of endothelial cell lipoxygenase in the oxidative modification of low density lipoprotein. Proc. Natl. Acad. Sci. U.S.A. 1989, 86 1040-1050.
37. 2+ channel blockers (Nifedipine, Diltiazem and Verapamil) against the toxicity of oxidized low density lipoproteins to cultured lymphoid cells. Br. J. Pharmacol. 1992, 107, 738-744.
38. Trash, M. A.; Wilson, M. E.; Van Dyke, K. The generation of chemiluminescence by phagocytic cells. Methods Enzymol. 1978, 57, 462-494.
39. Hopkins, N. K.; Oglesby, T. D.; Bundy, G. L.; Gosman, R. R. Biosynthesis and metabolism of 15-hydroperoxy-5,8,11,13-eicos-a-tetraenoic acid by human umbilical vein endothelial cells. J. Biol. Chem. 1994, 259, 14048-14053
40. + induced contraction in rat aorta. Eur. J. Pharmacol. 1991, 205, 49-54.
41. Ianelli, S.; Nardelli, M.; Belletti, D.; Jamart-Grégoire, B.; Caubère, C.; Caubère, P. Conformation at the amide N atom of 1-carboxamide indole derivatives. Acta Crystallogr. 1995, C51, 1341-1345.
42. Cook, J. W.; London, J. D.; McCloskey, P. Chemistry of the Mitragyna genus II. Synthesis of 7-methoxy-2-methyl-and 7-methoxy-1,2-dimethyl-β-carboline. J. Chem. Soc. 1951, 1203-1207.
43. Yagi, K. Lipid peroxides and human diseases. Chem. Phys. Lipids 1987, 45, 337-351.
44. Escargueil-Blanc, I.; Salvayre, R.; Negre-Salvayre, A. Necrosis and apoptosis induced by oxidized LDL occur through two calcium-dependent pathways in lymphoblastoid cells. FASEB J. 1994, 8, 1075-1080.
45. Price, P.; McMillan, T. J. Use of tetrazolium assay for measuring the response of human tumor cells to ionizing radiations. Cancer Res. 1989, 50, 1392-1396.