(S)-N-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)-N-methylamine | 442128-85-0

• 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: (S)-N-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)-N-methylamine
• 英文别名: (2S)-2-(methylamino)-3-(4-phenylmethoxyphenyl)propan-1-ol
• CAS: 442128-85-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: JABXWRJJVKFUIR-INIZCTEOSA-N

物化性质

• 熔点：
  106.0-107.5 °C
• 沸点：
  443.0±35.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)-N-methylamine 在 palladium on activated charcoal ammonium hydroxide 、 碘苯二乙酸 、 氢气 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-methylspiro[1,4-diazabicyclo[3.2.1]octane-7,4'-cyclohexa-2,5-diene]-1',3-dione
  参考文献：
  名称：

  对映纯（-）-TAN1251A的简便合成

  摘要：

  对映纯（-）-TAN1251A（毒蕈碱M 1受体拮抗剂）的正式总合成是通过使用双（乙酰氧基）碘代苯作为芳香族化合物的关键步骤，通过螺环碳氮键的形成而实现的。

  DOI：

  10.1016/s0040-4039(02)00296-4
• 作为产物：
  描述：

  (S)-3-(4-hydroxyphenyl)-2-[(ethoxycarbonyl)amino]-1-propanoic acid methyl ester 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-N-(1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)-N-methylamine
  参考文献：
  名称：

  对映纯（-）-TAN1251A的简便合成

  摘要：

  对映纯（-）-TAN1251A（毒蕈碱M 1受体拮抗剂）的正式总合成是通过使用双（乙酰氧基）碘代苯作为芳香族化合物的关键步骤，通过螺环碳氮键的形成而实现的。

  DOI：

  10.1016/s0040-4039(02)00296-4

文献信息

• [EN] MAO-B SELECTIVE INHIBITOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF AND USES THEREOF<br/>[FR] COMPOSÉS INHIBITEURS À SÉLECTIVITÉ MAO-B, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET UTILISATIONS CORRESPONDANTES
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2015027324A1

  公开（公告）日：2015-03-05

  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。
• Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions
  作者：Chu-Pei Xu、Zhen-Hua Xiao、Bi-Qin Zhuo、Yu-Huang Wang、Pei-Qiang Huang

  DOI：10.1039/c0cc01487g

  日期：——

  We report a mild and environmentally benign method for the synthesis of tertiary amines using alcohols as the alkylating reagents. Not only secondary amines such as piperazines but also amino acids and amino alcohols can be N-alkylated selectively. For N,O-benzyl protected amino alcohols, both N,O-de-benzylation and N-methylation were achieved in one-pot.

  我们报告了使用醇作为烷基化试剂合成叔胺的温和，环保的方法。不仅仲胺如哌嗪而且氨基酸和氨基醇都可以被选择性地N-烷基化。对于N，O-苄基保护的氨基醇，一锅中同时实现了N，O-去苄基化和N-甲基化。
• 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。
• 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
  作者：Ronan Gealageas、Alice Devineau、Pauline P. L. So、Catrina M. J. Kim、Jayakumar Surendradoss、Christian Buchwalder、Markus Heller、Verena Goebeler、Edith M. Dullaghan、David S. Grierson、Edward E. Putnins

  DOI：10.1021/acs.jmedchem.7b01588

  日期：2018.8.23

  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.