3-[4-(14-Hydroxy-tetradecyloxy)-benzyl]-4H-[1,2,4]oxadiazol-5-one | 310869-77-3

• 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-(14-Hydroxy-tetradecyloxy)-benzyl]-4H-[1,2,4]oxadiazol-5-one
• 英文别名: 3-[[4-(14-hydroxytetradecoxy)phenyl]methyl]-4H-1,2,4-oxadiazol-5-one
• CAS: 310869-77-3
• 化学式: C₂₃H₃₆N₂O₄
• 分子量: 404.55
• InChiKey: KJOWEMMXCQBBPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[4-(14-Hydroxy-tetradecyloxy)-benzyl]-4H-[1,2,4]oxadiazol-5-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 1.0h， 以55%的产率得到14-[4-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-ylmethyl)-phenoxy]-tetradecanoic acid
  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：

  14-溴-1-十四烷醇 在 盐酸 、 sodium hydroxide 、 盐酸羟胺 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.0h， 生成 3-[4-(14-Hydroxy-tetradecyloxy)-benzyl]-4H-[1,2,4]oxadiazol-5-one
  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

文献信息

• [EN] PHOSPHOLIPASE A2-SPECIFIC INHIBITING COMPOUNDS<br/>[FR] COMPOSES INHIBITEURS SPECIFIQUES DE LA PHOSPHOLIPASE A2
  申请人：UNIV PARIS 7 DENIS DIDEROT

  公开号：WO2000071118A1

  公开（公告）日：2000-11-30

  La présente invention concerne de nouveaux composés inhibiteurs spécifiques de la phospholipase A2 répondant à la formule générale (I). Ces nouveaux composés sont susceptibles d'agir sur les PLA2 et sont avantageusement des composés inhibiteurs spécifiques de la PLA2snp totalement inactifs sur la PLA2 pancréatique. La présente invention concerne également un procédé de préparation de ces nouveaux composés, des compositions les contenant et leur utilisation notamment en thérapie de pathologies inflammatoires et en cosmétique.
• 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.