4-<(2-quinolinylmethyl)thio>phenol | 125439-43-2

• 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-<(2-quinolinylmethyl)thio>phenol
• 英文别名: 4-(Quinolin-2-ylmethylsulfanyl)phenol
• CAS: 125439-43-2
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: LKBBWSRKHXVBRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<(2-quinolinylmethyl)thio>phenol 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-[3-(4-(2-quinolylmethylthio)phenoxy)propyl]tetrazole
  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-羟基苯硫酚 、 2-氯甲基喹啉盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到4-<(2-quinolinylmethyl)thio>phenol
  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

• 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：——
• Quinoline derivatives, their use in the treatment of hypersensitive ailments and a pharmaceutical composition containing the same
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：EP0315399B1

  公开（公告）日：1996-01-10
• THERAPEUTIC USES OF QUINOLINE DERIVATIVES
  申请人：Aventis Pharmaceuticals Products Inc.

  公开号：EP1030665A1

  公开（公告）日：2000-08-30
• EP1030665A4
  申请人：——

  公开号：EP1030665A4

  公开（公告）日：2002-11-27
• US4920132A
  申请人：——

  公开号：US4920132A

  公开（公告）日：1990-04-24