4-(benzyloxy)-2-<(6-methyl-6-cyanoheptyl)oxy>ethylbenzene | 152609-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(benzyloxy)-2-<(6-methyl-6-cyanoheptyl)oxy>ethylbenzene
• 英文别名: 7-(2-Ethyl-5-phenylmethoxyphenoxy)-2,2-dimethylheptanenitrile
• CAS: 152609-40-0
• 化学式: C₂₄H₃₁NO₂
• 分子量: 365.516
• InChiKey: VOLCIQGWCDHYEG-UHFFFAOYSA-N

物化性质

• 沸点：
  523.7±45.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-2-<(6-methyl-6-cyanoheptyl)oxy>ethylbenzene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 以98%的产率得到1-bromo-2-benzyloxy-4-(6-methyl-6-cyanoheptyloxy)-5-ethylbenzene
  参考文献：
  名称：

  邻苯酚：有效和口服的白三烯B4受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00076a029
• 作为产物：
  描述：

  6-cyano-1-chloro-6-methylheptane 在 三乙基硅烷 、 potassium carbonate 、 三氟乙酸 、 potassium iodide 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(benzyloxy)-2-<(6-methyl-6-cyanoheptyl)oxy>ethylbenzene
  参考文献：
  名称：

  邻苯酚：有效和口服的白三烯B4受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00076a029

文献信息

• o-Phenylphenols: potent and orally active leukotriene B4 receptor antagonists
  作者：Michael J. Sofia、Paul Floreancig、Nicholas J. Bach、S. Richard Baker、Sandra L. Cockerham、Jerome H. Fleisch、Larry L. Froelich、William T. Jackson、Philip Marder

  DOI：10.1021/jm00076a029

  日期：1993.11
• US5563164A
  申请人：——

  公开号：US5563164A

  公开（公告）日：1996-10-08
• Synthetic and Structure/Activity Studies on Acid-Substituted 2-Arylphenols: Discovery of 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic Acid, a High-Affinity Leukotriene B4 Receptor Antagonist
  作者：J. Scott Sawyer、Nicholas J. Bach、S. Richard Baker、Ronald F. Baldwin、Peter S. Borromeo、Sandra L. Cockerham、Jerome H. Fleisch、Paul Floreancig、Larry L. Froelich

  DOI：10.1021/jm00022a006

  日期：1995.10

  Structural derivatives of LY255283 have been studied as receptor antagonists of leukotriene B-4. Substitution of the 2-hydroxyacetophenone subunit of 1 (LY255283) with a 2-arylphenol group provided entry into several new series that feature various mono- and diacidic core functionality. These new analogues, the subject of a broad structure-activity investigation, displayed significantly increased in vitro and in vivo activity as receptor antagonists of LTB(4). A series of diaryl ether carboxylic acids demonstrated especially interesting activity and led to the discovery of compound 43b, 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic acid (LY293111), a 2-arylphenol-substituted diaryl ether carboxylic acid which displayed potent binding to human neutrophils (IC50 = 17 +/- 14.6 nM) and guinea pig lung membranes (IC50 6.6 +/- 0.71 nM), inhibition of LTB(4)-induced expression of the CD11b/CD18 receptor on human neutrophils (IC50 - 3.3 +/- 0.81 nM), and inhibition of LTB(4)-induced contraction of guinea pig lung parenchyma (pK(B) = 8.7 +/- 0.16). In vivo, 43b demonstrated potent activity in inhibiting LTB(4)-induced airway obstruction in the guinea pig when dosed by the oral (ED(50) = 0.40 mg/kg) or intravenous (ED(50) = 0.014 mg/kg) routes. A specific LTB(4) receptor antagonist, 43b had little effect on inhibiting contractions of guinea pig lung parenchyma induced by leukotriene D-4 (LTD(4)), histamine, carbachol, or U46619. Compound 43b has been chosen as a clinical candidate and is currently in phase I studies for a variety of inflammatory diseases.