(R)-(1-(4-benzyloxy)phenyl)-N-methylpropan-2-amine

• 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: (R)-(1-(4-benzyloxy)phenyl)-N-methylpropan-2-amine
• 英文别名: (R)-1-(4-(benzyloxy)phenyl)-N-methylpropan-2-amine；(2R)-N-methyl-1-(4-phenylmethoxyphenyl)propan-2-amine
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: QBXSHZSWFLOPBX-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(1-(4-benzyloxy)phenyl)-N-methylpropan-2-amine 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 tert-butyl (R)-N-(1-(4-((3-chlorobenzyl)oxy)phenyl)propan-2-yl)-N-methylglycinate
  参考文献：
  名称：

  Development of Novel Monoamine Oxidase-B (MAO-B) Inhibitors with Reduced Blood–Brain Barrier Permeability for the Potential Management of Noncentral Nervous System (CNS) Diseases

  摘要：

  Studies indicate that MAO-B is induced in peripheral inflammatory diseases. To target peripheral tissues using MAO-B inhibitors that do not permeate the blood brain barrier (BBB) the MAO-B-selective inhibitor deprenyl was remodeled by replacing the terminal acetylene with a CO2H function, and incorporating a para-OCH2Ar motif (compounds 10a-s). Further, in compound 32 the C-2 side chain corresponded to CH2CN. In vitro, 10c, 10j, 10k, and 32 were identified as potent reversible MAO-B inhibitors, and all four compounds were more stable than deprenyl in plasma, liver microsomal, and hepatocyte stability assays. In vivo, they demonstrated greater plasma bioavailability. Assessment of in vitro BBB permeability showed that compound 10k is a P-glycoprotein (P-gp) substrate and 10j displayed mild interaction. Importantly, compounds 10c, 10j, 10k, and 32 displayed significantly reduced BBB permeability after intravenous, subcutaneous, and oral administration. These polar MAO-B inhibitors are pertinent leads for evaluation of efficacy in noncentral nervous system (CNS) inflammatory disease models.

  DOI：

  10.1021/acs.jmedchem.7b01588
• 作为产物：
  描述：

  L-酪氨酸甲酯盐酸盐 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 水 、 碳酸氢钠 、 potassium carbonate 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 (R)-(1-(4-benzyloxy)phenyl)-N-methylpropan-2-amine
  参考文献：
  名称：

  [EN] MAO-B SELECTIVE INHIBITOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF AND USES THEREOF
  [FR] COMPOSÉS INHIBITEURS À SÉLECTIVITÉ MAO-B, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET UTILISATIONS CORRESPONDANTES

  摘要：

  本文描述了一系列具有公式I结构的化合物，用于抑制MAO并用于治疗屏障疾病、肥胖、实体上皮细胞肿瘤转移、糖尿病、自身免疫和炎症性疾病或心脏代谢紊乱。

  公开号：

  WO2015027324A1

文献信息

• MAO-B Selective Inhibitor Compounds, Pharmaceutical Compositions Thereof and Uses Thereof
  申请人：THE UNIVERSITY OF BRTISH COLUMBIA

  公开号：US20160207878A1

  公开（公告）日：2016-07-21

  Described herein are a series of compounds having the structure of Formula I: for use in the inhibition of MAO and uses thereof for the treatment of a barrier disease, obesity, solid epithelial cell tumor metastasis, diabetes, an auto-immune and inflammatory disease or a cardiometabolic disorder.

  本文描述了一系列具有I式结构的化合物，用于抑制MAO并用于治疗障碍性疾病、肥胖症、实体上皮细胞肿瘤转移、糖尿病、自身免疫和炎症性疾病或心脏代谢紊乱的用途。
• MAO-B selective inhibitor compounds, pharmaceutical compositions thereof and uses thereof
  申请人：The University of British Columbia

  公开号：US10196345B2

  公开（公告）日：2019-02-05

  Described herein are a series of compounds having the structure of Formula I: for use in the inhibition of MAO and uses thereof for the treatment of a barrier disease, obesity, solid epithelial cell tumor metastasis, diabetes, an auto-immune and inflammatory disease or a cardiometabolic disorder.

  本文描述了一系列具有式 I 结构的化合物： 用于抑制 MAO 及其在治疗屏障疾病、肥胖症、实体上皮细胞肿瘤转移、糖尿病、自身免疫性和炎症性疾病或心脏代谢紊乱方面的用途。
• MAO-B SELECTIVE INHIBITOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF AND USES THEREOF
  申请人：The University of British Columbia

  公开号：EP3039009B1

  公开（公告）日：2019-05-01
• MAO-B INHIBITORS USEFUL FOR TREATING OBESITY
  申请人：McElroy Francis John

  公开号：US20070004683A1

  公开（公告）日：2007-01-04

  The invention provides novel compounds of formulae I and II: that are monoamine oxidase-B inhibitors, which can be useful in treating obesity, diabetes, and/or cardiometabolic disorders (e.g., hypertension, dyslipidemias, high blood pressure, and insulin resistance).
• US7956220B2
  申请人：——

  公开号：US7956220B2

  公开（公告）日：2011-06-07