3-(4-tetradecyloxybenzyl)-4H-1,2,4-oxadiazol-5-one | 310869-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-tetradecyloxybenzyl)-4H-1,2,4-oxadiazol-5-one
• 英文别名: PMS1062；3-{[4-(Tetradecyloxy)phenyl]methyl}-4,5-dihydro-1,2,4-oxadiazol-5-one；3-[(4-tetradecoxyphenyl)methyl]-4H-1,2,4-oxadiazol-5-one
• CAS: 310869-68-2
• 化学式: C₂₃H₃₆N₂O₃
• 分子量: 388.55
• InChiKey: ANLYQPBTEGWYHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-tetradecyloxybenzyl)-4H-1,2,4-oxadiazol-5-one 、 重氮甲烷 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以73%的产率得到
  参考文献：
  名称：

  Inhibition of secretory phospholipase A2. 2-Synthesis and structure–activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme

  摘要：

  We have recently reported the discovery of a series of specific inhibitors of human group IIA phospholipase A(2) (hGIIA PLA(2)) to display promising in vitro and in vivo properties. Here we describe the influence of different structural modifications on the specificity and potency against hGIIA PLA(2) versus porcine group IB PLA(2). The SAR results, as well as the log P and pK(a) values of oxadiazolone determined in this work, provide important information towards the comprehension of the mode of action of this kind of compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.016
• 作为产物：
  描述：

  对羟基苯乙腈 在 吡啶 、 sodium hydroxide 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成 3-(4-tetradecyloxybenzyl)-4H-1,2,4-oxadiazol-5-one
  参考文献：
  名称：

  分泌型磷脂酶A2的抑制作用。从4-十四烷基氧基苯甲relationship开始的1-设计，合成和结构-活性关系研究，以获得II组sPLA2s的特异性抑制剂。

  摘要：

  从GI和GII PLA2s的非特异性抑制剂4-十四烷氧基苯甲m（PMS815）开始，我们在这项工作中报告了通过设计，合成和不同种类的PMS815衍生物的结构活性关系研究发现特异性。领先的化合物4,5-二氢-3-（4-十四烷基氧基苄基）-1,2,4-4H-恶二唑-5-酮（9b，PMS1062）对3个II类PLA2表现出微摩尔IC50，对4个PLA2则无活性在两种体外酶分析条件下，第I组和第III组酶。它还能够阻断HepG2细胞系中LPS和IL-6诱导的PLA2-II活性，并且在两种不同的细胞系（A549和LLC-PK1）中测试PMS1062的浓度高达100 microM时，未观察到细胞毒性。 。

  DOI：

  10.1016/j.ejmech.2005.03.027

文献信息

• EXTRACELLULAR MITOCHONDRIAL COMPONENTS FOR DETECTING INFLAMMATORY REACTIONS AND CONDITIONS
  申请人：Université Laval

  公开号：EP3055690A1

  公开（公告）日：2016-08-17
• Extracellular Mitochondrial Components for Detecting Inflammatory Reactions and Conditions
  申请人：UNIVERSITÉ LAVAL

  公开号：US20160258950A1

  公开（公告）日：2016-09-08

  The present disclosure highlights the relationship between extracellular mitochondrial components, optionally in combination with the secreted phospholipase A 2 -IIA and/or an auto-antibody, and in vivo as well as in vitro and inflammatory reactions/conditions, especially those released as a result of the degradation of a platelet. The present disclosure provides methods for determining the presence of inflammatory mediators, for limiting inflammatory reactions/conditions, for the diagnosis inflammatory reactions/conditions, for screening therapeutics for the treatment and/or the alleviation of symptoms of inflammatory reactions/conditions based on the detection or modulation of the level of these extracellular mitochondrial components.
• US9945853B2
  申请人：——

  公开号：US9945853B2

  公开（公告）日：2018-04-17
• [EN] EXTRACELLULAR MITOCHONDRIAL COMPONENTS FOR DETECTING INFLAMMATORY REACTIONS AND CONDITIONS<br/>[FR] COMPOSANTS MITOCHONDRIAUX EXTRACELLULAIRES POUR DÉTECTION DE RÉACTIONS ET D'ÉTATS INFLAMMATOIRES
  申请人：UNIVERSITÉ LAVAL

  公开号：WO2015051466A1

  公开（公告）日：2015-04-16

  The present disclosure highlights the relationship between extracellular mitochondrial components, optionally in combination with the secreted phospholipase A2-IIA and/or an auto-antibody, and in vivo as well as in vitro and inflammatory reactions/conditions, especially those released as a result of the degradation of a platelet. The present disclosure provides methods for determining the presence of inflammatory mediators, for limiting inflammatory reactions/conditions, for the diagnosis inflammatory reactions/conditions, for screening therapeutics for the treatment and/or the alleviation of symptoms of inflammatory reactions/conditions based on the detection or modulation of the level of these extracellular mitochondrial components.
• Inhibition of secretory phospholipase A2. 2-Synthesis and structure–activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme
  作者：Chang-Zhi Dong、Azali Ahamada-Himidi、Stéphanie Plocki、Darina Aoun、Mohamed Touaibia、Nadia Meddad-Bel Habich、Jack Huet、Catherine Redeuilh、Jean-Edouard Ombetta、Jean-Jacques Godfroid、France Massicot、Françoise Heymans

  DOI：10.1016/j.bmc.2005.01.016

  日期：2005.3

  We have recently reported the discovery of a series of specific inhibitors of human group IIA phospholipase A(2) (hGIIA PLA(2)) to display promising in vitro and in vivo properties. Here we describe the influence of different structural modifications on the specificity and potency against hGIIA PLA(2) versus porcine group IB PLA(2). The SAR results, as well as the log P and pK(a) values of oxadiazolone determined in this work, provide important information towards the comprehension of the mode of action of this kind of compounds. (c) 2005 Elsevier Ltd. All rights reserved.