Design and synthesis of sodium (beta R*, gamma S*)-4-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl] thio]-gamma-hydroxy-beta-methylbenzenebutanoate: a novel, selective, and orally active receptor antagonist of leukotriene D4.

Design and synthesis of sodium (beta R, gamma S)-4-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl] thio]-gamma-hydroxy-beta-methylbenzenebutanoate: a novel, selective, and orally active receptor antagonist of leukotriene D4.

作者信息

Young R N, Bélanger P, Champion E, DeHaven R N, Denis D, Ford-Hutchinson A W, Fortin R, Frenette R, Gauthier J Y, Gillard J

出版信息

J Med Chem. 1986 Sep;29(9):1573-6. doi: 10.1021/jm00159a003.

DOI:10.1021/jm00159a003

PMID:3746809

Abstract

摘要

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Design and synthesis of sodium (beta R*, gamma S*)-4-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl] thio]-gamma-hydroxy-beta-methylbenzenebutanoate: a novel, selective, and orally active receptor antagonist of leukotriene D4.

J Med Chem. 1986 Sep;29(9):1573-6. doi: 10.1021/jm00159a003.

L-649,923, sodium (beta S*, gamma R*)-4-(3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propylthio)- gamma-hydroxy-beta-methylbenzenebutanoate, a selective, orally active leukotriene receptor antagonist.L-649,923，（βS*，γR*）-4-（3-（4-乙酰基-3-羟基-2-丙基苯氧基）-丙硫基）-γ-羟基-β-甲基苯丁酸酯钠，一种选择性口服活性白三烯受体拮抗剂。

Can J Physiol Pharmacol. 1986 Aug;64(8):1068-75. doi: 10.1139/y86-183.

L-649,923, sodium (beta S*, gamma R*-4-(3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylthio)-gamma-hydroxy -beta-methylbenzenebutanoate. A selective, orally active leukotriene D4 receptor antagonist.L-649,923，钠（βS*，γR*-4-(3-(4-乙酰基-3-羟基-2-丙基苯氧基)丙基硫代)-γ-羟基-β-甲基苯丁酸酯）。一种选择性、口服活性白三烯D4受体拮抗剂。

Adv Prostaglandin Thromboxane Leukot Res. 1986;16:37-45.

L-648,051, sodium 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)- propylsulfonyl]-gamma-oxo-benzenebutanoate: a leukotriene D4 receptor antagonist.L-648,051，4-[3-(4-乙酰基-3-羟基-2-丙基苯氧基)-丙基磺酰基]-γ-氧代苯丁酸酯钠：一种白三烯D4受体拮抗剂。

Can J Physiol Pharmacol. 1986 Dec;64(12):1535-42. doi: 10.1139/y86-258.

Pharmacological properties of the orally active leukotriene antagonist [[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propyl]thio]-1,3,4- thiadiazol-2-yl]thio]acetic acid.

Arzneimittelforschung. 1988 May;38(5):682-5.

Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes.

J Med Chem. 1989 Apr;32(4):807-26. doi: 10.1021/jm00124a014.

Novel arylthio- and arylsulfonylpropyloxyacetophenones: design and synthesis of L-648,051 and L-649,923, potent antagonists of leukotriene D4.

Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:544-8.

Leukotriene receptor antagonists. 2. The [[(tetrazol-5-ylaryl)oxy]methyl]acetophenone derivatives.

J Med Chem. 1987 May;30(5):911-8. doi: 10.1021/jm00388a028.

L-648,051, a potent and specific aerosol active leukotriene D4 antagonist.L-648,051，一种强效且特异性的气溶胶活性白三烯D4拮抗剂。

Agents Actions Suppl. 1988;23:113-9. doi: 10.1007/978-3-0348-9156-1_7.

Synthesis and pharmacological characterization of 5-(2-dodecylphenyl)-4,6-dithianonanedioic acid and 5-[2-(8-phenyloctyl)phenyl]-4,6-dithianonanedioic acid: prototypes of a novel class of leukotriene antagonists.

J Med Chem. 1985 Sep;28(9):1145-7. doi: 10.1021/jm00147a004.

引用本文的文献

The contractile activities of lipoxin A4 and lipoxin B4 for guinea-pig airway tissues.脂氧素A4和脂氧素B4对豚鼠气道组织的收缩活性。

Br J Pharmacol. 1988 Oct;95(2):562-8. doi: 10.1111/j.1476-5381.1988.tb11677.x.

Inhibition of allergen-induced bronchoconstriction in hyperreactive rats as a model for testing 5-lipoxygenase inhibitors and leukotriene D4 receptor antagonists.以高反应性大鼠变应原诱导的支气管收缩抑制作为测试5-脂氧合酶抑制剂和白三烯D4受体拮抗剂的模型。

Agents Actions. 1987 Oct;22(1-2):69-74. doi: 10.1007/BF01968819.

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Design and synthesis of sodium (beta R, gamma S)-4-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl] thio]-gamma-hydroxy-beta-methylbenzenebutanoate: a novel, selective, and orally active receptor antagonist of leukotriene D4.