苯戊腈,4-羟基- | 129649-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 苯戊腈,4-羟基-
• 英文名称: 5-(4-Hydroxy-phenyl)-pentanenitrile
• 英文别名: 5-(4-Hydroxyphenyl)pentanenitrile
• CAS: 129649-96-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: OIDYVFFNWNQZOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯戊腈,4-羟基- 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 5-[4-(4-(2-quinolylmethyloxy)phenyl)butyl]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：

  (E)-5-(4-phenylmethoxyphenyl)pent-2-enenitrile 生成 苯戊腈,4-羟基-
  参考文献：
  名称：

  GALEMMO, ROBERT A.;JOHNSON, WILLIAM H. (JR);LEARN, KEITH S.;LEE, THOMAS D+, J. MED. CHEM., 33,(1990) N0, C. 2828-2841

  摘要：

  DOI：

文献信息

• Nitrogenous Educts through Oxidative Amidation of Phenols:  The Bimolecular Reaction
  作者：Sylvain Canesi、Denis Bouchu、Marco A. Ciufolini

  DOI：10.1021/ol048094v

  日期：2005.1.1

  [Reaction: see text] The elusive oxidative amidation of phenols to 4-aza-substituted dienones in the bimolecular mode may be achieved by treatment with iodobenzene diacetate ("DIB") in a mixture of hexafluoro-2-propanol and acetonitrile.

  [反应：见正文]在六氟-2-丙醇和乙腈的混合物中，用碘代苯二乙酸酯（“ DIB”）处理，可实现双分子模式下苯酚难以催化的氧化酰胺化成4-氮杂取代的二烯酮。
• The development of a novel series of (quinolin-2-ylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 3. Structural variation of the acidic side chain to give antagonists of enhanced potency
  作者：Robert A. Galemmo、William H. Johnson、Keith S. Learn、Thomas D. Y. Lee、Fu Chih Huang、Henry F. Campbell、Raymond Youssefyeh、Susan V. O'Rourke、Glenn Schuessler

  DOI：10.1021/jm00172a024

  日期：1990.10

  This paper is the third in a series outlining the development of orally active sulfido peptide leukotriene antagonists containing a (quinolin-2-ylmethoxy)phenyl moiety. In this work the systematic variation of the acid side chain substituents led to dramatic and reproducible changes in the oral activity of these compounds, presumably due to alterations in their pharmacokinetic properties. The most potent compound identified, 5-[4-[4-(quinolin-2-yl-methoxy)phenyl]-3-methylbutyl]tetrazole (32), represents a convergence of good in vitro antagonist activity and a 3-10-fold improvement in oral potency over the current clinical candidate 2. The new findings from these optimization studies are as follows: oxygen substitution in the acid side chain was not necessary for antagonist activity, in vitro and in vivo activity was enhanced by alkyl or phenyl substitution on the gamma-carbon of the acid side chain of para-substituted (quinolin-2-ylmethoxy)phenyl derivatives, and free rotation about the side chain carbon atom adjacent to the (quinolin-2-ylmethoxy)phenyl ring was required for activity. The lead compound of this report (32) is a competitive inhibitor of [3H]LTD4 binding to receptor membrane purified from guinea pig lung (Ki = 12 +/- 3 nM) and of the spasmogenic activity of LTC4, LTD4, and LTE4 in guinea pig lung strip. Dosed orally in guinea pigs, this compound blocks LTD4-induced bronchoconstriction (ED50 0.8 mg/kg) and antigen-induced systemic anaphylaxis (ED50 = 1.2 mg/kg).
• Synthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols
  作者：Marco A. Ciufolini、Sylvain Canesi、Malika Ousmer、Norbert A. Braun

  DOI：10.1016/j.tet.2006.01.111

  日期：2006.5

  We describe the development of a technique for the oxidative conversion of 4-alkyl phenols to derivatives of the corresponding 4-alkyl-4-amino-2,5-cyclohexanediones. This transformation, which was inspired by biogenetic considerations, constitutes a key step in the total syntheses of FR-901483, TAN-1251C, and cylindricine C. (c) 2006 Elsevier Ltd. All rights reserved.
• THERAPEUTIC USES OF PPAR MEDIATORS
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1267874A2

  公开（公告）日：2003-01-02
• US4920132A
  申请人：——

  公开号：US4920132A

  公开（公告）日：1990-04-24