2-benzyloxymethyl-1,3,4-oxadiazole | 23571-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyloxymethyl-1,3,4-oxadiazole
• 英文别名: 2-[(Benzyloxy)methyl]-1,3,4-oxadiazole；2-(phenylmethoxymethyl)-1,3,4-oxadiazole
• CAS: 23571-73-5
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD28145218
• 分子量: 190.202
• InChiKey: IGRWGGSQBLEZOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyloxymethyl-1,3,4-oxadiazole 、 7-[(4-benzyloxy-phenoxy)-N-methoxy-N-methyl]-heptane-carboxamide 在 正丁基锂 、 magnesium bromide ethyl etherate 、 cerium(III) chloride 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.25h， 以55%的产率得到7-(4-benzyloxy-phenoxy)-1-(5-benzyloxymethyl-1,3,4-oxadiazol-2-yl)-heptan-1-one
  参考文献：
  名称：

  [EN] MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY
  [FR] INHIBITEURS DE LA MONOACYLGLYCÉROL LIPASE DE MODULATION DE L'ACTIVITÉ CANNABINOÏDE

  摘要：

  揭示了抑制单酰基甘油脂酶（MGL）和脂肪酸酰胺水解酶（FAAH）作用的化合物和组合物，抑制MGL和FAAH的方法，调节大麻素受体的方法，以及治疗与调节大麻素受体相关的各种疾病的方法。

  公开号：

  WO2009052319A1
• 作为产物：
  描述：

  2-(苄氧基)乙酰肼 在 对甲苯磺酸 、 原甲酸三甲酯 作用下， 反应 3.0h， 以49%的产率得到2-benzyloxymethyl-1,3,4-oxadiazole
  参考文献：
  名称：

  WO2008/13963

  摘要：

  公开号：

文献信息

• FATTY ACID AMIDE HYDROLASE INHIBITORS
  申请人：Makriyannis Alexandros

  公开号：US20090306016A1

  公开（公告）日：2009-12-10

  Disclosed are compounds of formula R—X—Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CB1i and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.

  公开了一种R-X-Y式化合物，可用于抑制脂肪酸酰胺水解酶（FAAH）的作用。抑制脂肪酸酰胺水解酶（FAAH）将减缓FAAH水解作用引起的内源性大麻素配体的正常降解和失活，并允许更高水平的内源性大麻素配体保持存在。这些更高水平的内源性大麻素配体提供了对大麻素CB1i和CB2受体的增加刺激，并产生与大麻素受体激活相关的生理效应。它们还将增强其他外源性大麻素配体的效果，并允许它们在较低浓度下产生其效果，与不抑制脂肪酸酰胺水解酶（FAAH）作用的系统相比。因此，一种抑制脂肪酸酰胺水解酶（FAAH）对内源性大麻素配体失活的化合物可能会增加内源性大麻素的水平，从而增强大麻素受体的激活。因此，该化合物可能不直接调节大麻素受体，但通过增加内源性大麻素配体的水平间接刺激大麻素受体。它还可以增强其他外源性大麻素配体的效果和作用持续时间，这些配体被用于引发大麻素反应。
• Methods and Compounds for Modulating Cannabinoid Activity
  申请人：Makriyannis Alexandros

  公开号：US20110071178A1

  公开（公告）日：2011-03-24

  Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.

  本文披露了一些抑制单酰基甘油脂肪酶（MGL）和脂肪酸酰胺水解酶（FAAH）作用的化合物和组合物，抑制MGL和FAAH的方法，调节大麻素受体的方法，以及治疗与大麻素受体调节相关的各种疾病的方法。
• Fatty acid amide hydrolase inhibitors
  申请人：Makriyannis Alexandros

  公开号：US09102622B2

  公开（公告）日：2015-08-11

  Disclosed are compounds of formula R—X—Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CB1 and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.

  本发明揭示了化合物R-X-Y的公式，可用于抑制脂肪酸酰胺水解酶（FAAH）的作用。抑制脂肪酸酰胺水解酶（FAAH）将减缓FAAH水解对内源性大麻素配体的正常降解和失活，并允许更高水平的内源性大麻素配体保持存在。这些更高水平的内源性大麻素配体提供了对大麻素CB1和CB2受体的增强刺激，并产生与大麻素受体激活相关的生理效应。它们还增强了其他外源性大麻素配体的效果，并允许它们在相对于不抑制FAAH作用的系统中以较低的浓度产生其效果。因此，抑制脂肪酸酰胺水解酶（FAAH）对内源性大麻素配体的失活的化合物可能增加内源性大麻素的水平，从而增强大麻素受体的激活。因此，该化合物可能不直接调节大麻素受体，但通过增加内源性大麻素配体的水平间接刺激大麻素受体。它还可以增强其他外源性大麻素配体的作用和持续时间，以引发大麻素反应。
• MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY
  申请人：Makriyannis Alexandros

  公开号：US20110039874A1

  公开（公告）日：2011-02-17

  Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.

  公开了一种抑制单酰基甘油酯脂肪酶（MGL）和脂肪酸酰胺水解酶（FAAH）作用的化合物和组合物，抑制MGL和FAAH的方法，调节大麻素受体的方法，以及治疗与大麻素受体调节相关的各种疾病的方法。
• METHODS AND COMPOUNDS FOR MODULATING CANNABINOID ACTIVITY
  申请人：NORTHEASTERN UNIVERSITY

  公开号：EP2203058A1

  公开（公告）日：2010-07-07