2-(2-苯氧基乙氧基)乙胺 | 6338-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2-苯氧基乙氧基)乙胺
• 英文名称: 5-Phenoxy-3-oxa-1-pentanamin
• 英文别名: 2-(2-phenoxyethoxy)ethanamine；5-phenoxy-3-oxa-pentylamine
• CAS: 6338-54-1
• 化学式: C₁₀H₁₅NO₂
• mdl: MFCD09805738
• 分子量: 181.235
• InChiKey: NARMGECFWCSGGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-苯氧基乙氧基)乙胺 在 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.42h， 生成 (3-(3-carbamoyl-1H-pyrrol-1-yl)phenoxycarbonyl)(2-(2-phenoxyethoxy)ethyl)amine
  参考文献：
  名称：

  Discovery of Potent Inhibitors of Human and Mouse Fatty Acid Amide Hydrolases

  摘要：

  Fatty acid amide hydrolase (FAAH, EC 3.5.1.99) is the main enzyme catabolizing endocannabinoid fatty acid amides. FAAH inactivation promotes beneficial effects upon pain and anxiety without the side effects accompanying agonists of type-1 cannabinoid receptors. Aiming at discovering new selective FAAH inhibitors, we developed a series of compounds (5a-u) characterized by a functionalized heteroaromatic scaffold. Particularly, 5c and 5d were identified as extremely potent, noncompetitive, and reversible FAAH inhibitors endowed with a remarkable selectivity profile and lacking interaction with the hERG channels. In vivo antinociceptive activity was demonstrated for 5c, 5d, and 5n at a dose much lower than that able to induce either striatal and limbic stereotypies or anxiolytic activity, thus outlining their potential to turn into optimum preclinical candidates. Aiming at improving pharmacokinetic properties and metabolic stability of 5d, we developed a subset of nanomolar dialyzable FAAH inhibitors (5v-z), functionalized by specific polyethereal lateral chains and fluorinated aromatic rings.

  DOI：

  10.1021/jm300689c
• 作为产物：
  描述：

  2-(2-苯氧基乙氧基)乙醇 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-(2-苯氧基乙氧基)乙胺
  参考文献：
  名称：

  Discovery of Potent Inhibitors of Human and Mouse Fatty Acid Amide Hydrolases

  摘要：

  Fatty acid amide hydrolase (FAAH, EC 3.5.1.99) is the main enzyme catabolizing endocannabinoid fatty acid amides. FAAH inactivation promotes beneficial effects upon pain and anxiety without the side effects accompanying agonists of type-1 cannabinoid receptors. Aiming at discovering new selective FAAH inhibitors, we developed a series of compounds (5a-u) characterized by a functionalized heteroaromatic scaffold. Particularly, 5c and 5d were identified as extremely potent, noncompetitive, and reversible FAAH inhibitors endowed with a remarkable selectivity profile and lacking interaction with the hERG channels. In vivo antinociceptive activity was demonstrated for 5c, 5d, and 5n at a dose much lower than that able to induce either striatal and limbic stereotypies or anxiolytic activity, thus outlining their potential to turn into optimum preclinical candidates. Aiming at improving pharmacokinetic properties and metabolic stability of 5d, we developed a subset of nanomolar dialyzable FAAH inhibitors (5v-z), functionalized by specific polyethereal lateral chains and fluorinated aromatic rings.

  DOI：

  10.1021/jm300689c

文献信息

• Heimann,U. et al., Chemische Berichte, 1979, vol. 112, p. 1392 - 1399
  作者：Heimann,U. et al.

  DOI：——

  日期：——
• Procédé de préparation de tris(éther-amines) et tris(éther-amines) ainsi obtenues
  申请人：RHONE-POULENC SPECIALITES CHIMIQUES

  公开号：EP0018884B1

  公开（公告）日：1981-11-04
• AZETIDINONE DERIVATIVES FOR THE TREATMENT OF ATHEROSCLEROSIS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0840725A1

  公开（公告）日：1998-05-13
• ANIONIC EXCHANGE-HYDROPHOBIC MIXED MODE CHROMATOGRAPHY RESINS
  申请人：BIO-RAD LABORATORIES, INC.

  公开号：US20210069692A1

  公开（公告）日：2021-03-11

  Chromatography resins having anionic exchange-hydrophobic mixed mode ligands and methods of using such resins are provided.
• [EN] AZETIDINONE DERIVATIVES FOR THE TREATMENT OF ATHEROSCLEROSIS<br/>[FR] DERIVES DE L'AZETIDINONE POUR LE TRAITEMENT DE L'ATHEROSCLEROSE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1997002242A1

  公开（公告）日：1997-01-23

  (EN) Azetidinone compounds of formule (I) in which: R1 and R2, which may be the same or different, is each selected from hydrogen, halogen or C(1-8)alkyl; R4 and R5 which may be the same or different is each selected from hydrogen, C(1-6)alkyl, C(2-6)alkenyl, aryl, aryl(C1-4)alkyl and heteroaryl(C1-4)alkyl each of which may be optionally substituted or R4 and R5 may be linked together to form the remainder of a (C3-7)cycloalkyl ring; X is a linker group; Y is an optionally substituted aryl group; Z is oxygen and R3 is C(1-8)alkyl, C(3-8)cycloalkyl, C(3-8)cycloalkylC(1-6)alkyl, heteroaryl, heteroaryl(C1-4)alkyl, aryl, or aryl(C1-4)alkyl, each of which may be optionally substituted or Z is S(O)n in which n is 0, 1 or 2 and R3 is C(1-8)alkyl, C(3-8)cycloalkyl, C(3-8)cycloalkylC(1-6)alkyl, aryl, aryl(C1-4)alkyl, heteroaryl, or heteroaryl(C1-4)alkyl, each of which may be optionally substituted are inhibitors of the enzyme Lp PLA2 and are of use in therapy, in particular treating atherosclerosis.(FR) L'invention concerne les composés de l'azétidinone présentant la formule (I). Dans cette formule, R1 et R2 peuvent être identiques ou différents, et sont chacun sélectionnés parmi de l'hydrogène, de l'halogène ou de l'alkyle (C1-8); R4 et R5 peuvent être semblables ou différents et sont chacun sélectionnés parmi de l'hydrogène, de l'alkyle (C1-6), de l'alcényle (C2-6), de l'aryle, de l'arylalkyle (C1-4) et de l'hétéroarylalkyle (C1-4), qui peuvent être tous éventuellement substitués, ou R4 et R5 peuvent être liés ensemble pour former le reste d'un noyau de cycloalkyle (C3-7); X est un groupe de liaison; Y est un groupe aryle éventuellement substitué; Z est de l'oxygène et R3 est de l'alkyle (C1-8), du cycloalkyle (C3-8), du cycloalkyle(C3-8)alkyle(C1-6), de l'hétéroaryle, de l'hétéroarylalkyle (C1-4), de l'aryle, ou de l'arylalkyle (C1-4) qui peuvent être tous éventuellement substitués, ou Z désigne à S(O)n où n vaut 0, 1 ou 2 et R3 est de l'alkyle (C1-8), du cycloalkyle (C3-8), du cycloalkyle (C3-8), de l'aryle, de l'alkyle (C1-4) d'aryle, de l'hétéroaryle, ou de l' hétéroarylalkyle (C1-4), qui peuvent tous être éventuellement substitués. Ces composés sont des inhibiteurs de l'enzyme Lp PLA2 et sont particulièrement utiles dans le traitement de l'athérosclérose.