1-(benzyloxy)-4-(4-bromobutoxy)benzene | 90816-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(benzyloxy)-4-(4-bromobutoxy)benzene
• 英文别名: 1-Benzyloxy-4-(4-bromobutoxy)benzene；1-(4-bromobutoxy)-4-phenylmethoxybenzene
• CAS: 90816-68-5
• 化学式: C₁₇H₁₉BrO₂
• 分子量: 335.241
• InChiKey: XTRQBDWFYYGGHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C(Solvent: Hexane)
• 沸点：
  443.0±30.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-4-(4-bromobutoxy)benzene 在 sodium sulfite 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.25h， 以51%的产率得到4-(4-benzyloxyphenoxy)butanesulfonyl chloride
  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：

  1,4-二溴丁烷 、 4-苄氧基苯酚 在 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 1-(benzyloxy)-4-(4-bromobutoxy)benzene
  参考文献：
  名称：

  新型苯氧基烷基吡啶鎓肟作为沙林和VX替代物抑制胆碱酯酶的脑穿透激活剂的功效

  摘要：

  吡啶鎓肟是强亲核试剂，许多是有机磷酸酶抑制胆碱酯酶（ChE）的有效活化剂。然而，当前的肟再活化剂在穿越血脑屏障和再活化完整生物中的脑ChE方面是无效的。我们的实验室已经开发了一系列取代的苯氧基烷基吡啶鎓肟（美国专利9,227,937 B2），目的是鉴定能有效跨越血脑屏障的活化剂。发现该系列的前35个在体外具有相似的特征沙林替代品（邻苯二甲酰亚胺基异丙基甲基膦酸酯，PIMP）或VX替代品（硝基苯基乙基甲基膦酸酯，NEMP）在牛脑制剂中抑制ChE活化剂的功效，如先前在大鼠脑制剂中观察到的。这些新型肟中的许多已经显示出能够降低用高致死剂量的沙林替代品（硝基苯基异丙基甲基膦酸酯，NIMP）或VX替代NEMP处理的大鼠大脑中ChE抑制水平的能力。肟给药后2小时的再活化水平高达35％，而目前批准的治疗药物2-PAM并未降低脑ChE抑制作用。另外，有证据显示几种更有效的新型肟可减轻癫痫样行为，但2-PA

  DOI：

  10.1016/j.cbi.2016.07.004

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。
• Copper-Catalyzed Cross-Coupling Reaction of Allyl Boron Ester with 1°/2°/3°-Halogenated Alkanes
  作者：Guang-Zu Wang、Jian Jiang、Xiao-Song Bu、Jian-Jun Dai、Jun Xu、Yao Fu、Hua-Jian Xu

  DOI：10.1021/acs.orglett.5b01612

  日期：2015.8.7

  The cross-coupling reaction of allyl boron ester with 1°/2°/3°-halogenated alkanes in the presence of copper has been developed for the first time, which provides a mild and efficient method for the construction of saturated C(sp3)–C(sp3) bonds. This protocol shows excellent compatibility with the nonactivated primary, secondary, and even tertiary halogenated alkanes under mild conditions.

  首次开发了烯丙基硼酸酯与1°/ 2°/ 3°卤代烷烃在铜存在下的交叉偶联反应，这为构建饱和C（sp 3）–C（sp 3）键。该方案在温和条件下与未活化的伯，仲，甚至叔卤代烷烃显示出优异的相容性。
• 2-substituted piperidine analogs and their use as subtype-selective NMDA
  申请人：Warner-Lambert Company

  公开号：US06124317A1

  公开（公告）日：2000-09-26

  Novel 2-substituted piperidine analogs, pharmaceutical compositions containing the same and the method of using 2-substituted piperidine analogs as selectively active antagonists of N-methyl-D-aspartatc (NMDA) receptor subtypes for treating conditions such as stroke, cerebral ischemia, central nervous system trauma, hypoglycemia, anxiety, convulsions, amioglycoside antibiotics-induced hearing loss, migraine headaches, chronic pain, glaucoma, CMV retinitis, psychosis, urinary incontinence, opioid tolerance or withdrawal, or neurodegenerative disorders, such as lathyrism, Alzheimer's Disease, Parkinsonism and Huntington's Disease are described.

  小说中描述了2-取代哌啶类似物、含有这些类似物的药物组合物，以及使用2-取代哌啶类似物作为选择性活性拮抗剂的方法，用于治疗中风、脑缺血、中枢神经系统创伤、低血糖、焦虑、抽搐、氨基糖苷类抗生素引起的听力损失、偏头痛、慢性疼痛、青光眼、巨细胞病毒性视网膜炎、精神病、尿失禁、阿片类耐受性或戒断症状，或神经退行性疾病，如拉锥病、阿尔茨海默病、帕金森病和亨廷顿病。
• Compound
  申请人：——

  公开号：US20040019016A1

  公开（公告）日：2004-01-29

  There is provided a compound of Formula I 1 wherein each T is independently selected from H, hydrocarbyl, —F—R, and a bond with one of D, E, P or Q, or together with one of P and Q forms a ring; Z is a suitable atom the valency of which is m; D, E and F are each independently of each other an optional linker group, wherein when Z is nitrogen E is other than CH 2 and C═O; P, Q and R are independently of each other a ring system; and at least Q comprises a sulphamate group.

  提供了一个式I1的化合物，其中每个T分别选自H、烃基、—F—R和与D、E、P或Q中的一个之一形成键，或者与P和Q中的一个一起形成环；Z是一个适当的原子，其价数为m；D、E和F分别独立于彼此，是可选的连接基团，其中当Z是氮时，E不是CH2和C═O；P、Q和R独立于彼此，是一个环系统；至少Q包含一个磺酰胺基团。