2-(biphenyl-4-yl)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone

• 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)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone
• 英文别名: 2-Biphenyl-4-yl-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone；1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(4-phenylphenyl)ethanone
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: JFQMGEPSMYFWMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(biphenyl-4-yl)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone 在 三氟化硼乙醚 、 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到2-(2-Biphenyl-4-yl-ethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  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 、 6,7-二甲氧基-1,2,3,4-四氢异喹啉盐酸盐 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-(biphenyl-4-yl)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone
  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

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.