2-(3,4-dimethoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide | 13397-02-9

• 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: 2-(3,4-dimethoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
• 英文别名: 3,4-dimethoxyphenyl-N-[2-(4-methoxyphenyl)ethyl]acetamide；N-(4-Methoxy-phenylethyl)-3,4-dimethoxyphenylacetamid
• CAS: 13397-02-9
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: OUOFCQDYLMMMBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 甲基叔丁基醚 、 水 为溶剂， 反应 3.0h， 生成 6,7-dimethoxy-2-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A New Class of Selective and Potent 7-Dehydrocholesterol Reductase Inhibitors

  摘要：

  We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.

  DOI：

  10.1021/jm3006096
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 、 2-(4-甲氧苯基)乙胺 以 neat (no solvent) 为溶剂， 反应 0.5h， 以99%的产率得到2-(3,4-dimethoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
  参考文献：
  名称：

  芳基乙酸与 2-芳基-乙胺反应的微波辅助酰胺化

  摘要：

  摘要 在无溶剂条件下，通过芳基乙酸和 2-芳基-乙胺的微波辅助缩合，以几乎定量的产率合成了 25 种酰胺。N-芳乙基-芳基乙酰酰胺是相应异喹啉衍生物的中间体。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2011.642925

文献信息

• Microwave-Assisted Amidation of Arylacetic Acids by Reaction with 2-Aryl-ethylamines
  作者：Alajos Grün、Mátyás Milen、Tamás Földesi、Péter Ábrányi-Balogh、László Drahos、György Keglevich

  DOI：10.1080/00397911.2011.642925

  日期：2013.6.3

  Abstract Twenty-five amides were synthesized in almost quantitative yields by microwave-assisted condensation of arylacetic acids and 2-aryl-ethylamines under solventless conditions. The N-arylethyl-arylacetylamides are intermediates of the corresponding isoquinoline derivates. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to

  摘要 在无溶剂条件下，通过芳基乙酸和 2-芳基-乙胺的微波辅助缩合，以几乎定量的产率合成了 25 种酰胺。N-芳乙基-芳基乙酰酰胺是相应异喹啉衍生物的中间体。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• A New Class of Selective and Potent 7-Dehydrocholesterol Reductase Inhibitors
  作者：Aline Horling、Christoph Müller、Richard Barthel、Franz Bracher、Peter Imming

  DOI：10.1021/jm3006096

  日期：2012.9.13

  We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.
• A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids
  作者：Dennis Pollok、Luca M. Großmann、Torsten Behrendt、Till Opatz、Siegfried R. Waldvogel

  DOI：10.1002/chem.202201523

  日期：2022.9.6

  Highly pharmaceutically relevant Amaryllidaceae alkaloids have been accessed by a versatile electro-organic key transformation, including a precursor of the acetylcholinesterase inhibitor galantamine, used as FDA-approved drug for the treatment of Alzheimer's disease. Spirodienone-type intermediates were obtained in a regioselective and sustainable anodic key transformation from nature-derived starting

  高度药学相关的石蒜科生物碱已通过多功能电有机关键转化获得，其中包括乙酰胆碱酯酶抑制剂加兰他敏的前体，该药物被 FDA 批准用作治疗阿尔茨海默病的药物。螺二烯酮型中间体是通过区域选择性和可持续的阳极关键转化从天然原料中获得的