2-Benzylamino-1-(4-benzyloxy-phenyl)-propan-1-one | 62634-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Benzylamino-1-(4-benzyloxy-phenyl)-propan-1-one
• 英文别名: 2-(Benzylamino)-1-[4-(benzyloxy)phenyl]propan-1-one；2-(benzylamino)-1-(4-phenylmethoxyphenyl)propan-1-one
• CAS: 62634-51-9
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: FUOFOOUYEIGWGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Benzylamino-1-(4-benzyloxy-phenyl)-propan-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 对羟基去甲麻黄碱
  参考文献：
  名称：

  一系列取代对羟基苯乙醇胺的新型子宫舒张活性的合成和评价。

  摘要：

  通过缩合外消旋1-（对羟基苯基）合成新型外消旋1-（4-羟基苯基）-2- [3-（取代苯氧基）-2-羟基-1-丙基]氨基丙烷-1-醇盐酸盐（9a-h）。 ）-2-氨基丙-1-醇盐酸盐（6）在无水碳酸钾存在下于DMF中与取代的芳氧基甲基环氧乙烷（8a-h）混合，然后与干燥的氯化氢气体反应。对离体大鼠子宫的体外子宫松弛活性和妊娠大鼠体内的子宫松弛活性进行了评估。使用大鼠子宫组织匀浆通过cAMP [3H]分析研究了它们的cAMP释放潜能，并评估了狗的心脏刺激潜能。所有化合物在体外均表现出有效的子宫松弛活性，并显着延迟了妊娠大鼠的分娩。除9b和9c外，它们的cAMP释放潜能均高于盐酸异苏比林。最后，与盐酸异苏必林相比，这些化合物的心脏刺激潜力微不足道。

  DOI：

  10.1016/j.bmc.2006.06.006
• 作为产物：
  描述：

  4‘-苄氧基苯丙酮 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 2-Benzylamino-1-(4-benzyloxy-phenyl)-propan-1-one
  参考文献：
  名称：

  一系列取代对羟基苯乙醇胺的新型子宫舒张活性的合成和评价。

  摘要：

  通过缩合外消旋1-（对羟基苯基）合成新型外消旋1-（4-羟基苯基）-2- [3-（取代苯氧基）-2-羟基-1-丙基]氨基丙烷-1-醇盐酸盐（9a-h）。 ）-2-氨基丙-1-醇盐酸盐（6）在无水碳酸钾存在下于DMF中与取代的芳氧基甲基环氧乙烷（8a-h）混合，然后与干燥的氯化氢气体反应。对离体大鼠子宫的体外子宫松弛活性和妊娠大鼠体内的子宫松弛活性进行了评估。使用大鼠子宫组织匀浆通过cAMP [3H]分析研究了它们的cAMP释放潜能，并评估了狗的心脏刺激潜能。所有化合物在体外均表现出有效的子宫松弛活性，并显着延迟了妊娠大鼠的分娩。除9b和9c外，它们的cAMP释放潜能均高于盐酸异苏比林。最后，与盐酸异苏必林相比，这些化合物的心脏刺激潜力微不足道。

  DOI：

  10.1016/j.bmc.2006.06.006

文献信息

• Synthesis and evaluation of uterine relaxant activity for a novel series of substituted p-hydroxyphenylethanolamines
  作者：C.L. Viswanathan、A.S. Chaudhari

  DOI：10.1016/j.bmc.2006.06.006

  日期：2006.10

  Novel racemic 1-(4-hydroxyphenyl)-2-[3-(substituted phenoxy)-2-hydroxy-1-propyl]aminopropan-1-ol hydrochlorides (9a-h) were synthesized by condensing racemic 1-(p-hydroxyphenyl)-2-aminopropan-1-ol hydrochloride (6) with substituted aryloxymethyloxiranes (8a-h) in DMF in presence of anhydrous potassium carbonate and then reacting with dry hydrogen chloride gas. They were evaluated for uterine relaxant

  通过缩合外消旋1-（对羟基苯基）合成新型外消旋1-（4-羟基苯基）-2- [3-（取代苯氧基）-2-羟基-1-丙基]氨基丙烷-1-醇盐酸盐（9a-h）。 ）-2-氨基丙-1-醇盐酸盐（6）在无水碳酸钾存在下于DMF中与取代的芳氧基甲基环氧乙烷（8a-h）混合，然后与干燥的氯化氢气体反应。对离体大鼠子宫的体外子宫松弛活性和妊娠大鼠体内的子宫松弛活性进行了评估。使用大鼠子宫组织匀浆通过cAMP [3H]分析研究了它们的cAMP释放潜能，并评估了狗的心脏刺激潜能。所有化合物在体外均表现出有效的子宫松弛活性，并显着延迟了妊娠大鼠的分娩。除9b和9c外，它们的cAMP释放潜能均高于盐酸异苏比林。最后，与盐酸异苏必林相比，这些化合物的心脏刺激潜力微不足道。
• Toxicity of the amphetamine metabolites 4-hydroxyamphetamine and 4-hydroxynorephedrine in human dopaminergic differentiated SH-SY5Y cells
  作者：R. Feio-Azevedo、V.M. Costa、L.M. Ferreira、P.S. Branco、F.C. Pereira、M.L. Bastos、F. Carvalho、J.P. Capela

  DOI：10.1016/j.toxlet.2017.01.012

  日期：2017.3

  Amphetamine (AMPH) is a psychostimulant used worldwide by millions of patients in the clinical treatment of attention deficit hyperactivity disorder, narcolepsy or even obesity, and is also a drug of abuse. 4-Hydroxynorephedrine (4-OHNE) and 4-hydroxyamphetamine (4-OHAMPH) are two major metabolites known to persist in the brain longer than AMPH. The contribution of AMPH metabolites for its neurotoxicity is undetermined.We evaluated the toxicity of AMPH and its metabolites 4-OHNE and 4-OHAMPH, obtained by chemical synthesis, in human dopaminergic differentiated SH-SY5Y neurons. Cells were exposed to AMPH (concentration range 0-5 mM) or 4-OHAMPH or 4-OHNE (concentration range 0-10 mM) for 24 or 48 h, and the viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MIT) and lactate dehydrogenase (LDH) leakage assays.Results showed that for both AMPH and the metabolites a concentration-dependent toxicity was observed. The toxic concentration 50% (TC50) for AMPH and 4-OHNE following 24 h exposure was circa 3.5 mM and 8 mM, respectively. For 4-OHAMPH the TC50 was not reached in the tested concentration range. N-acetyl cysteine, cycloheximide, L-carnitine, and methylphenidate were able to reduce cell death induced by AMPH TC50. Acridine orange/ethidium bromide staining showed evident signs of late apoptotic cells and necrotic cells following 24 h exposure to AMPH 3.50 mM. The 4-OHAMPH metabolite at 8.00 mM originated few late apoptotic cells, whereas 4-OHNE at 8.00 mM resulted in late apoptotic cells and necrotic cells, in a scenario similar to AMPH.In conclusion, the AMPH metabolite 4-OHNE is more toxic than 4-OHAMPH, nonetheless both are less toxic than the parent compound in vitro. The most toxic metabolite 4-OHNE has longer permanence in the brain, rendering likely its contribution for AMPH neurotoxicity. (C) 2017 Elsevier B.V. All rights reserved.