4-<(4-hydroxyphenyl)thio>butyronitrile | 125439-47-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-<(4-hydroxyphenyl)thio>butyronitrile
• 英文别名: 4-(4-Hydroxyphenyl)sulfanylbutanenitrile
• CAS: 125439-47-6
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: SFTWCYMYPAMFHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<(4-hydroxyphenyl)thio>butyronitrile 在 sodium hydroxide 、 sodium azide 、 氯化铵 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 2-{4-[3-(1H-Tetrazol-5-yl)-propylsulfanyl]-phenoxymethyl}-quinoline
  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 、 4-溴丁腈 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以81%的产率得到4-<(4-hydroxyphenyl)thio>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

• A method of enhancing a luminescent reaction, luminometric assay and kits for use in the same
  申请人：SANYO CHEMICAL INDUSTRIES, LTD.

  公开号：EP0505198A1

  公开（公告）日：1992-09-23

  A chemiluminescent reaction, which may be utilized for immunoassay, carried out by reaction of 2,3-dihydro-1,4-phthalazinedione or its derivative, a peroxidase, and an oxidant, is enhanced by conducting it in the presence of a phenolic compound such as (4-cyanomethylthio)phenol. Especially, it is preferred that (4-cyanomethylthio)phenol is added to each of luminol, horseradish peroxidase, and a hydrogen peroxide to provide a significantly enhanced and stabilised luminescent reaction.

  通过 2,3-二氢-1,4-酞嗪二酮或其衍生物、过氧化物酶和氧化剂的反应进行的化学发光反应可用于免疫测定，在酚类化合物如（4-氰基甲硫基）苯酚的存在下进行化学发光反应可增强该反应。特别优选的是，在发光酚、辣根过氧化物酶和过氧化氢中各加入（4-氰基甲硫基）苯酚，以显著增强和稳定发光反应。
• 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：——
• US5424194A
  申请人：——

  公开号：US5424194A

  公开（公告）日：1995-06-13