1-(2-hydroxy-3-propyl-4-{[4-(3-cyanobenzoyl)phenoxy]methyl}phenyl)ethanone | 118909-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-hydroxy-3-propyl-4-{[4-(3-cyanobenzoyl)phenoxy]methyl}phenyl)ethanone
• 英文别名: 3-[4-[(4-Acetyl-3-hydroxy-2-propylphenyl)methoxy]benzoyl]benzonitrile
• CAS: 118909-05-0
• 化学式: C₂₆H₂₃NO₄
• 分子量: 413.473
• InChiKey: RQFNPAXGCSEWEX-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  622.9±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3-propyl-4-{[4-(3-cyanobenzoyl)phenoxy]methyl}phenyl)ethanone 生成 1-[2-hydroxy-3-propyl-4-({4-[4-(1H-tetrazol-5-yl)-benzoyl]phenoxy}methyl)phenyl]ethanone
  参考文献：
  名称：

  CARR, F. P.;DILLARD, ROBERT D.;MCCULLOUGH, DORIS E.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-甲氧基苯甲酰基)苯甲腈 在 三氯化铝 、 potassium tert-butylate 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 1-(2-hydroxy-3-propyl-4-{[4-(3-cyanobenzoyl)phenoxy]methyl}phenyl)ethanone
  参考文献：
  名称：

  (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists

  摘要：

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.

  DOI：

  10.1021/jm00113a014

文献信息

• Leukotriene antagonists and use thereas
  申请人：Eli Lilly and Company

  公开号：US04853398A1

  公开（公告）日：1989-08-01

  This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.

  这项发明提供了苯乙烯衍生物，这些衍生物是白三烯拮抗剂，以及这些衍生物的配方，以及使用这些衍生物治疗由白三烯过度释放引起的疾病的方法。
• CARR, F. P.;DILLARD, ROBERT D.;MCCULLOUGH, DORIS E.
  作者：CARR, F. P.、DILLARD, ROBERT D.、MCCULLOUGH, DORIS E.

  DOI：——

  日期：——
• Improvements in or relating to leukotriene antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0288189B1

  公开（公告）日：1992-11-11
• US4853398A
  申请人：——

  公开号：US4853398A

  公开（公告）日：1989-08-01
• (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists
  作者：Robert D. Dillard、Richard A. Hahn、Doris McCullough、F. Patrick Carr、Lynn E. Rinkema、Carlos R. Roman、Jerome H. Fleisch

  DOI：10.1021/jm00113a014

  日期：1991.9

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.