4-<4-(hydroxymethyl)phenoxy>butyronitrile | 125439-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-<4-(hydroxymethyl)phenoxy>butyronitrile
• 英文别名: 4-(3-cyanopropyloxy)benzyl alcohol；Butanenitrile, 4-[4-(hydroxymethyl)phenoxy]-；4-[4-(hydroxymethyl)phenoxy]butanenitrile
• CAS: 125439-56-7
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD11149451
• 分子量: 191.23
• InChiKey: WAEZZCAFZLZKKH-UHFFFAOYSA-N

物化性质

• 沸点：
  380.0±22.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<4-(hydroxymethyl)phenoxy>butyronitrile 在 sodium azide 、 sodium hydride 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 2-{4-[3-(1H-Tetrazol-5-yl)-propoxy]-benzyloxymethyl}-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：

  3-溴丙腈 、 对羟基苯甲醇 在 potassium iodide 、 potassium carbonate 作用下， 以 正己烷 、 水 、 丁酮 为溶剂， 生成 4-<4-(hydroxymethyl)phenoxy>butyronitrile
  参考文献：
  名称：

  Pyrazoles as human non-pancreatic secretory phospholipase A.sub.2

  摘要：

  揭示了一类新型吡唑并公开了利用这些化合物抑制sPLA.sub.2介导的脂肪酸释放，用于治疗诸如感染性休克等疾病的方法。

  公开号：

  US05972972A1

文献信息

• [EN] PYRAZOLES AS HUMAN NON-PANCREATIC SECRETORY PHOSPHOLIPASE A2 INHIBITORS<br/>[FR] PYRAZOLES UTILISES COMME INHIBITEURS DE PHOSPHOLIPASE A2 HUMAINE SECRETOIRE NON PANCERATIQUE
  申请人：ELI LILLY AND COMPANY

  公开号：WO1998024437A1

  公开（公告）日：1998-06-11

  (EN) A class of novel pyrazoles is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.(FR) Nouvelle classe de pyrazoles et utilisation de ces composés pour inhiber la libération d'acides gras induite par sPLA2 dans le traitement de maladies telles que le choc septique.

  （EN）公开了一类新型吡唑以及此类化合物用于抑制sPLA2介导的脂肪酸释放以治疗感染性休克等病症的用途。（FR）吡唑的新类别及其在治疗严重疾病中的应用。
• Pyrazoles as human non-pancreatic secretory phospholipase A2 inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP0846687B1

  公开（公告）日：2001-08-08
• 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：——
• US5972972A
  申请人：——

  公开号：US5972972A

  公开（公告）日：1999-10-26
• Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 1. Initial structure-activity relationships
  作者：Raymond D. Youssefyeh、Ernest Magnien、Thomas D. Y. Lee、Wan Kit Chan、Clara J. Lin、Robert A. Galemmo、William H. Johnson、Jenny Tan、Henry F. Campbell

  DOI：10.1021/jm00166a016

  日期：1990.4

  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.