5-bromo-1-(4-hydroxyphenyl)pentane | 103502-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-bromo-1-(4-hydroxyphenyl)pentane
• 英文别名: 4-(5-bromo-pentyl)-phenol；4-(5-Brom-pentyl)-phenol；5-Bromo-1-(4-hydroxy-phenyl)-pentane；4-(5-bromopentyl)phenol
• CAS: 103502-23-4
• 化学式: C₁₁H₁₅BrO
• 分子量: 243.143
• InChiKey: ZEAPQCRJAJJJPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-1-(4-hydroxyphenyl)pentane 在 氟化铵 、 三氟化硼乙醚 、 potassium carbonate 、 1,2-乙二硫醇 、 sodium sulfite 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 9.25h， 生成 5-(4-hydroxyphenyl)pentanesulfonylfluoride
  参考文献：
  名称：

  Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  Sulfonyl fluorides are known to inhibit esterases. Early work, from our laboratory has identified hexadecyl sulfonylfluoride (AM374) as a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase (FAAH). We now report on later generation sulfonyl fluoride analogs that exhibit potent and selective inhibition of FAAH. Using recombinant rat and human FAAH, we show that 5-(4-hydroxyphenyl)pentanesulfonyl fluoride (AM3506) has similar inhibitory activity for both the rat and the human enzyme, while dilution assays and mass spectrometry analysis suggest that the compound is a covalent modifier for FAAH and inhibits its action in an irreversible manner. Our SAR results are highlighted by molecular docking of key analogs.

  DOI：

  10.1021/jm301205j
• 作为产物：
  描述：

  (Z)-1-(4-methoxyphenyl)-5-phenoxypent-1-ene 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， -30.0~20.0 ℃ 、206.85 kPa 条件下， 反应 8.0h， 生成 5-bromo-1-(4-hydroxyphenyl)pentane
  参考文献：
  名称：

  Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  Sulfonyl fluorides are known to inhibit esterases. Early work, from our laboratory has identified hexadecyl sulfonylfluoride (AM374) as a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase (FAAH). We now report on later generation sulfonyl fluoride analogs that exhibit potent and selective inhibition of FAAH. Using recombinant rat and human FAAH, we show that 5-(4-hydroxyphenyl)pentanesulfonyl fluoride (AM3506) has similar inhibitory activity for both the rat and the human enzyme, while dilution assays and mass spectrometry analysis suggest that the compound is a covalent modifier for FAAH and inhibits its action in an irreversible manner. Our SAR results are highlighted by molecular docking of key analogs.

  DOI：

  10.1021/jm301205j
• 作为试剂：
  描述：

  1-(4-methoxyphenyl)-5-phenoxypentane 、 三溴化硼 在 5-bromo-1-(4-hydroxyphenyl)pentane 作用下， 以 二氯甲烷 为溶剂， 以The title compound (9.4) was isolated as a viscous liquid的产率得到5-bromo-1-(4-hydroxyphenyl)pentane
  参考文献：
  名称：

  MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY

  摘要：

  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。

  公开号：

  US20110039874A1

文献信息

• Dual modulation of endocannabinoid transport and fatty-acid amide hydrolase for treatment of excitotoxicity
  申请人：Bahr Ben A.

  公开号：US20100234379A1

  公开（公告）日：2010-09-16

  The endocannabinoid transporter and FAAH are sites of modulation that allow pharmacological enhancement of protective endocannabinergic signals. Selective inhibitors of the transporter and inhibitors of FAAH caused additive augmentation of endogenous signaling events mediated by the cannabinoid CB1 receptor. Disruption of such signals has been shown to prevent neuronal maintenance processes and increase vulnerability to brain damage. Here, blocking endocannabinoid inactivation enhanced cannabinergic activity and ameliorated cellular disturbances associated with excitotoxicity. Modulating the endocannabinoid system in this way also prevented excitotoxic behavioral abnormalities including memory impairment. Collectively, these results indicate that increasing endocannabinoid responses by inhibiting the endocannabinoid transported and/or the inhibiting FAAH leads to molecular, cellular, and functional protection against excitotoxic insults like stroke and traumatic brain injury.

  内源大麻素转运体和FAAH是调节的位点，允许药物增强保护性内源大麻素信号。选择性转运体抑制剂和FAAH抑制剂导致通过大麻素CB1受体介导的内源信号事件的加成增强。破坏这种信号已被证明可以防止神经维持过程并增加对脑损伤的脆弱性。在这里，阻断内源大麻素失活增强了大麻活性，并改善了与兴奋毒性相关的细胞紊乱。以这种方式调节内源大麻素系统还可以预防兴奋毒性行为异常，包括记忆障碍。总的来说，这些结果表明，通过抑制内源大麻素转运体和/或抑制FAAH来增加内源大麻素反应，可以在分子、细胞和功能上保护免受像中风和创伤性脑损伤等兴奋毒性侵害。
• [EN] MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY<br/>[FR] INHIBITEURS DE LA MONOACYLGLYCÉROL LIPASE DE MODULATION DE L'ACTIVITÉ CANNABINOÏDE
  申请人：UNIV NORTHEASTERN

  公开号：WO2009052319A1

  公开（公告）日：2009-04-23

  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.

  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。
• Eine Desaromatisierungsreaktion. Synthese von Spiro-[5:5]-undecadien-(1,4)-on-(3). Vorläufige Mitteilung
  作者：André S. Dreiding

  DOI：10.1002/hlca.19570400628

  日期：——

  By heating a dilute solution of the potassium salt of 5-(p-hydroxyphenyl)-1-bromopentane (I) it is possible to obtain spiro-[5:5]-undeca-1,4-diene-3-one (II) in good yield. During this intramolecular alkylation a phenolic ring is changed into a cyclohexadienone. The term desaromatisation is applied to this reaction.

  通过加热5-（对羟基苯基）-1-溴戊烷（I）的钾盐的稀溶液，可以获得螺-[5：5] -undeca-1,4-二烯-3-酮（II） ），产量高。在该分子内烷基化过程中，酚环变成环己二烯酮。术语脱芳构作用适用于该反应。
• 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。