A novel series of 2,6,7-substituted 2,3-dihydro-1,4-benzodioxin and 2,6,7-substituted 1,4-benzodioxin derivatives as lipid peroxidation inhibitors. Structure-activity relationships for high inhibition of human low-density lipoprotein peroxidation

Journal of Medicinal Chemistry

Volumn 44, Issue 23, 2001, Pages 3904-3914

  Thiery V ^a,b   Coudert, G ^a   Bizot Espiard, J G ^c   Pfeiffer, B ^d   Renard, P ^d   Lindenbaum, A ^e   Guillaumet, G ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b UNIVERSITÉ DE LA ROCHELLE   (France)

^c HÔPITAL ANTOINE BÉCLÈRE   (France)

^d INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

^e ADIR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZODIOXIN DERIVATIVE; 2,3 DIHYDRO 1,4 BENZODIOXIN; CALCIUM ANTAGONIST; COPPER; FLUNARIZINE; LOW DENSITY LIPOPROTEIN; PROBUCOL; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM ANTAGONISM; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HYPOLIPEMIA; HYPOXIA; LIPID PEROXIDATION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTILIPEMIC AGENTS; ANTIOXIDANTS; AORTA, THORACIC; CALCIUM CHANNEL BLOCKERS; COPPER; DIOXINS; DIOXOLES; HUMANS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; LIPOPROTEINS, VLDL; MALE; MICE; PIPERAZINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035829451     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0108045     Document Type: Article

References (60)

1. Role of oxidized low-density lipoprotein in atherogenosis
2. Effect of oral supplementation with D-α-tecopherol on the vitamin E content of human low-density lipoprotein and resistance to oxidation
3. The oxidation hypothesis of atherosclerosis
4. Low density lipoprotein oxidation and its pathobiological significance
5. Oxidation of low density lipoproteins in the pathogenesis of atherosclerosis
6. Is lipid peroxidation relevant for atherogenesis?
7. Biochemical and cytotoxic characteristics of an in vivo circulating oxidized low-density lipoprotein (LDL)
8. Role of oxidized LDL and antioxidants in atherosclerosis
9. Receptors for oxidized low density lipoprotein
10. Structure of low density lipoprotein (LDL) particles: Basis for understanding molecular changes in modified LDL
11. Oxidants and antioxidants in atherogenesis. An appraisal
12. Clinical trials of antioxidants in atherosclerosis: Are we doing the right thing?
13. Antioxidants in the prevention of human atherosclerosis. Summary of the proceedings of a national heart, lung and blood institute workshop: September 5-6, 1991
14. Review of human studies on oxidative damage and antioxidant protection related to cardiovascular diseases
15. Probucol: Pharmacology and clinical application
16. The effect of probucol on the progression of atherosclerosis in mature Watanabe heritable hyperlipidaemic rabbits
17. Antioxidant activity of probucol and its analogues in hypercholesterolemic Watanabe rabbits
18. 6-Hydroxychroman-2-carboxylic acids: Novel antioxidants
19. 2-(Aminomethyl)chromans that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma and ischemia
20. The trolox analog, U-78517 F attenuates hyposcic injury in isolated cardiac myocyts
21. Benzylamine antioxidant: Relationships between structure peroxyl radical scavenging lipid peroxidation inhibition and cytoprotection
22. Novel indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives. Structure-activity relationships for high inhibition of human LDL peroxidation
23. 2-Benzo-dioxinylaminoethanols: A new class of β-adrenergic blocking and antihypertensive agents
24. Alpha-adrenoreceptor reagents. 3. Synthesis of some 2-substituted 1,4-benzodioxans as selective presynaptic alpha 2-adrenoreceptor antagonists
25. 2,4-Diamino-6,7-dimethoxyquinazolines. 1. 2-[4-(1,4-Benzodioxan-2-ylcarbonyl)piperazin-l-yl] derivatives as alpha 1-adrenoceptor antagonists and antihypertensive agents
26. Alpha- and beta-adrenoceptors: From the gene to the clinic. 2. Structure-activity relationships and therapeutic applications
27. Synthesis and α,β-adrenergic blocking potency of 2,3-dihydro-1,4-benzodioxin derivatives
28. Structure-activity relationships in 1,4-benzodioxan-related compounds. 6. Role of the dioxane unit on selectivity for alpha(1)-adrenoreceptor subtypes
29. Alpha 1-adrenoreceptor antagonists bearing a quinazoline or a benzodioxane moiety
30. Graphics computer-aided receptor mapping as a predictive tool for drug design: Development of potent selective and stereospecific ligands for the 5-HT1A receptor
31. Serotonergic properties of spiroxatrine enantiomers
32. N-substituted-(2,3-dihydro-1,4 -benzodioxin-2yl)methylamine derivatives as D-2 antagonists/5-HT1A partial agonists with potential as atypical antipsychotic agents
33. Synthesis and evaluation of 2-(arylimino)imidazoles as alpha 2-adrenergic agonists
34. Derivatives of 2-[[N-(aminocarbonyl)-N-hydroxyamino]methyl]-1,4-benzodioxan as orally active 5-lipoxygenase inhibitors
35. The definite structure of americanin-A and hydnocarpin
36. Structures of americanol A and isoamericanol A having a neurotrophic property from the seeds of Phytolacca americana
37. A convenient synthesis of (±)-3-methoxybenzodioxane-4,9,9′-triol neolignan, and methyl ethers of isoamericanol A and isoamericanin A
38. Convenient syntheses of neurotrophic americanol A and isoamericanol A by HRP catalyzed oxidative coupling of caffeic acid
39. Total synthesis of (±)-sinaiticin
40. First asymmetric synthesis of chiral 1,4-benzodioxane lignans
41. New substituted benzodioxins-2-substituted with amide or thioamide group. Antioxidant for lipoproteins antilipemic agents anticholesterol agents
42. Convenient synthesis of 2-substituted-6 or 7-acylated-1,4-benzodioxin or 2,3-dihydro-1,4-benzodioxin derivatives
43. Convenient synthesis of 6-amino-1,4-benzodioxin-2-carboxylic acid ethyl ester
44. Influence of cardioprotective cyclooxygenase and lipoxygenase inhibitors on peroxidative injury to myocardial-membrane phospholipid
45. Antiperoxidant effects of dihydropyridine calcium antagonists
46. Calcium channel blockers and atherosclerosis
47. Antiperoxidative actions of calcium antagonists and atherogenesis
48. 2+ channel blockers (nifedipine diltiazem and verapamil) against the toxicity of oxidized low density lipoproteins to cultured lymphoid cells
49. Phenothiazines as lipid peroxidation inhibitors and cytoprotective agents
50. Modified conditions for efficient Baeyer-Villiger oxidation with m-CPBA
51. Synthese de benzodioxines-1,4
52. 2-(Aminomethyl) phenols a new class of saluretic agents. Effect of nuclear substitution
53. A new method for synthesis peptides: Activation of the carboxyl group with dicyclohexylcarbodiimide using 1-hydroxybenzotriazoles as additives
54. Studies on organophosphorous compounds-XL. Reactions of ketones with 2,4-bis(4-methoxyphenyl)1,3,2,4-dithiadiphosphetane-2,4-disulfide
55. Fractionation of charge-modified low density lipoproteins by fast protein liquid chromatography
56. Lipids peroxides and human diseases
57. + induced contraction in rat aorta
58. Systemic administration of MK-801 protects against ischemia-induced hippocampal neurodegeneration in the gerbil