4-<4-(2-quinolinylmethoxy)phenoxy>butyronitrile | 114497-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-<4-(2-quinolinylmethoxy)phenoxy>butyronitrile
• 英文别名: 4-[4-(2-quinolylmethyloxy)phenoxy]butyronitrile；4-[4-(quinolin-2-ylmethoxy)phenoxy]butanenitrile
• CAS: 114497-65-3
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: HFSASNCGYHBPSB-UHFFFAOYSA-N

物化性质

• 沸点：
  521.9±35.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-<4-(2-quinolinylmethoxy)phenoxy>butyronitrile 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 24.25h， 生成
  参考文献：
  名称：

  Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 1. Initial structure-activity relationships

  摘要：

  This series of reports describes the development of orally active, highly potent, specific antagonists of the peptidoleukotrienes containing a (2-quinolinylmethoxy)phenyl moiety. Described in this first report are the structure-activity relationships that led to a more than a 20-fold improvement of the potency and selectivity of the initial chemical lead (RG 5901). From this series of compounds, RG 7152 (16) was identified and selected for further evaluation in the clinic as an antiasthmatic agent. Compound 16 competitively inhibits [3H]LTD4 binding to membranes from guinea pig lung (Ki = 38 +/- 6 nM) and the spasmogenic activity of LTC4, LTD4, and LTE4 in parenchymal lung strips from guinea pigs. Unlike the original lead (RG 5901), compound 16 does not inhibit 5-lipoxygenase from guinea pig PMNs. Following oral administration to guinea pigs, 16 blocks LTD4-induced dermal permeability (ED50 = 6.9 mg/kg), LTD4-induced bronchoconstriction (ED50 = 1.1 mg/kg), antigen-induced bronchoconstriction (ED50 = 2.5 mg/kg), and anaphylactic-induced mortality (ED50 = 16 mg/kg). These studies on structure-activity relationships indicate that there is a requirement for an acidic function and the presence of the (2-quinolinylmethoxy)phenyl moiety in a specific geometric arrangement.

  DOI：

  10.1021/jm00166a016
• 作为产物：
  描述：

  4-苄氧基苯酚 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 40.0~60.0 ℃ 、310.27 kPa 条件下， 反应 32.5h， 生成 4-<4-(2-quinolinylmethoxy)phenoxy>butyronitrile
  参考文献：
  名称：

  Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 1. Initial structure-activity relationships

  摘要：

  This series of reports describes the development of orally active, highly potent, specific antagonists of the peptidoleukotrienes containing a (2-quinolinylmethoxy)phenyl moiety. Described in this first report are the structure-activity relationships that led to a more than a 20-fold improvement of the potency and selectivity of the initial chemical lead (RG 5901). From this series of compounds, RG 7152 (16) was identified and selected for further evaluation in the clinic as an antiasthmatic agent. Compound 16 competitively inhibits [3H]LTD4 binding to membranes from guinea pig lung (Ki = 38 +/- 6 nM) and the spasmogenic activity of LTC4, LTD4, and LTE4 in parenchymal lung strips from guinea pigs. Unlike the original lead (RG 5901), compound 16 does not inhibit 5-lipoxygenase from guinea pig PMNs. Following oral administration to guinea pigs, 16 blocks LTD4-induced dermal permeability (ED50 = 6.9 mg/kg), LTD4-induced bronchoconstriction (ED50 = 1.1 mg/kg), antigen-induced bronchoconstriction (ED50 = 2.5 mg/kg), and anaphylactic-induced mortality (ED50 = 16 mg/kg). These studies on structure-activity relationships indicate that there is a requirement for an acidic function and the presence of the (2-quinolinylmethoxy)phenyl moiety in a specific geometric arrangement.

  DOI：

  10.1021/jm00166a016

文献信息

• Quinolinyl ether or thioether tetrazoles as agents for the treatment of
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04874769A1

  公开（公告）日：1989-10-17

  This invention relates to certain quinolyl ether and thioether tetrazoles and their use as valuable pharmaceutical agents for the treatment of hypersensitive ailments, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and antiallergic properties.

  这项发明涉及某些喹诺醚和硫醚四唑，以及它们作为有价值的药用剂治疗过敏病症的用途，特别是作为脂氧合酶抑制剂和/或白三烯拮抗剂，具有抗炎和抗过敏特性。
• Aryl and heteroaryl ethers as agents for the treatment of hypersensitive
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04839369A1

  公开（公告）日：1989-06-13

  Aryl and Heteroaryl Ethers are used for their anti-inflammatory and anti-allergic properties.

  芳基和杂芳基醚因其抗炎和抗过敏特性而被使用。
• YOUSSEFYEH, RAYMOND;CHAKRABORTY, UTPAL;MAGNIEN, ERNEST;DESAI, ROHIT
  作者：YOUSSEFYEH, RAYMOND、CHAKRABORTY, UTPAL、MAGNIEN, ERNEST、DESAI, ROHIT

  DOI：——

  日期：——
• YOUSSEFYEH, RAYMOND D.;MAGNIEN, ERNEST;LEE, THOMAS D. Y.;CHAN, WAN-KIT;LI+, J. MED. CHEM., 33,(1990) N, C. 1186-1194
  作者：YOUSSEFYEH, RAYMOND D.、MAGNIEN, ERNEST、LEE, THOMAS D. Y.、CHAN, WAN-KIT、LI+

  DOI：——

  日期：——
• QUINOLINYL ETHER OR THIOETHER TETRAZOLES AS AGENTS FOR THE TREATMENT OF HYPERSENSITIVE AILMENTS
  申请人：RORER INTERNATIONAL (OVERSEAS) INC. (a Delaware corporation)

  公开号：EP0260305A1

  公开（公告）日：1988-03-23