2-(biphenyl-4-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide | 331436-06-7

• 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-(biphenyl-4-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• 英文别名: 2-Biphenyl-4-yl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide；N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-phenylphenyl)acetamide
• CAS: 331436-06-7
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: PXLSJPKOBLASLW-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  601.6±55.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(biphenyl-4-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 在 三氯氧磷 、 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 22.0h， 生成 6,7-bis-methoxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Discovery of Antiglioma Activity of Biaryl 1,2,3,4-Tetrahydroisoquinoline Derivatives and Conformationally Flexible Analogues

  摘要：

  Cultured rat astrocytes and C6 rat glioma were used as a differential screen for a variety of 1,2,3,4-tetrahydroisoquinoline (THI) derivatives. Compound 1 [1-(biphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline6,7-diol hydrochloride] selectively blocked the growth of C6 glioma leaving normal astrocytes relatively unaffected. The potential for clinical utility of 1 was further substantiated in human gliomas and other tumor cell lines. Preliminary SAR of this activity was characterized by synthesis and testing of several THI and conformationally flexible variants.

  DOI：

  10.1021/jm060020x
• 作为产物：
  描述：

  4-联苯乙酸 在 氯化亚砜 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 2-(biphenyl-4-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
  参考文献：
  名称：

  可见光介导的双氧氧化 1-苄基-3,4-二氢异喹啉：1-苯甲酰基异喹啉和 1-苯甲酰基-3,4-二氢异喹啉的可转换合成

  摘要：

  可见光介导的 1-苄基-3,4-二氢异喹啉 (1-BnDHIQs) 的无金属氧化，用于可切换制备多种 1-苯甲酰基异喹啉 (BzIQs) 和 1-苯甲酰基-3,4-二氢异喹啉(BzDHIQs) 是使用双氧作为氧化剂实现的。该方案为高效合成异喹啉生物碱提供了一条简便的途径。机理研究表明自由基途径和离子途径可能同时存在，这两种途径都通过共同的关键过氧化物中间体进行，产生氧化产物。

  DOI：

  10.1055/a-2160-8903

文献信息

• Substituted Tetrahydroisoquinoline Compounds for Cancer Therapy
  申请人：Miller D. Duane

  公开号：US20080033007A1

  公开（公告）日：2008-02-07

  Disclosed are compounds that are effective for selectively killing cancer cells. Compounds have been demonstrated to be especially effective for killing glioma cells, while exhibiting low toxicity to normal cells.

  本发明揭示了一些能够有效选择性杀死癌细胞的化合物。这些化合物已被证明对于杀死胶质瘤细胞特别有效，同时对正常细胞的毒性较低。
• Discovery of Antiglioma Activity of Biaryl 1,2,3,4-Tetrahydroisoquinoline Derivatives and Conformationally Flexible Analogues
  作者：Michael L. Mohler、Gyong-Suk Kang、Seoung-Soo Hong、Renukadevi Patil、Oleg V. Kirichenko、Wei Li、Igor M. Rakov、Eldon E. Geisert、Duane D. Miller

  DOI：10.1021/jm060020x

  日期：2006.9.1

  Cultured rat astrocytes and C6 rat glioma were used as a differential screen for a variety of 1,2,3,4-tetrahydroisoquinoline (THI) derivatives. Compound 1 [1-(biphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline6,7-diol hydrochloride] selectively blocked the growth of C6 glioma leaving normal astrocytes relatively unaffected. The potential for clinical utility of 1 was further substantiated in human gliomas and other tumor cell lines. Preliminary SAR of this activity was characterized by synthesis and testing of several THI and conformationally flexible variants.
• Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines
  作者：Hongli Wu、Haifeng Gan、Peipei Ma

  DOI：10.1055/a-2160-8903

  日期：2023.12

  oxidation of 1-benzyl-3,4-dihydroisoquinolines (1-BnDHIQs) for the switchable preparation of a wide range of 1-benzoylisoquinolines (BzIQs) and 1-benzoyl-3,4-dihydroisoquinolines (BzDHIQs) is realized using dioxygen as the oxidant. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigations suggest that a radical pathway and an ionic pathway

  可见光介导的 1-苄基-3,4-二氢异喹啉 (1-BnDHIQs) 的无金属氧化，用于可切换制备多种 1-苯甲酰基异喹啉 (BzIQs) 和 1-苯甲酰基-3,4-二氢异喹啉(BzDHIQs) 是使用双氧作为氧化剂实现的。该方案为高效合成异喹啉生物碱提供了一条简便的途径。机理研究表明自由基途径和离子途径可能同时存在，这两种途径都通过共同的关键过氧化物中间体进行，产生氧化产物。