2-benzo[1,3]dioxol-5-yl-N-[2-(4-methoxyphenyl)ethyl]acetamide | 1395084-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-benzo[1,3]dioxol-5-yl-N-[2-(4-methoxyphenyl)ethyl]acetamide
• 英文别名: 2-(2H-1,3-benzodioxol-5-yl)-N-[2-(4-methoxyphenyl)ethyl]acetamide；2-(1,3-benzodioxol-5-yl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
• CAS: 1395084-65-7
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: YTPCFQCBOWKELP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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-benzo[1,3]dioxol-5-yl-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 N-(4-methoxy-β-phenethyl)-6,7-methylenedioxy-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：

  胡椒乙酸 、 2-(4-甲氧苯基)乙胺 以 neat (no solvent) 为溶剂， 反应 0.5h， 以98%的产率得到2-benzo[1,3]dioxol-5-yl-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.