6,7-dimethoxy-1-[1-(3,4-dimethoxyphenyl)-2-(2-methoxymethoxyphenyl)-2-oxoethyl]isoquinoline | 190278-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-dimethoxy-1-[1-(3,4-dimethoxyphenyl)-2-(2-methoxymethoxyphenyl)-2-oxoethyl]isoquinoline
• 英文别名: 2-(6,7-Dimethoxyisoquinolin-1-yl)-2-(3,4-dimethoxyphenyl)-1-[2-(methoxymethoxy)phenyl]ethanone
• CAS: 190278-34-3
• 化学式: C₂₉H₂₉NO₇
• 分子量: 503.552
• InChiKey: WHIDAZOUPMGFII-UHFFFAOYSA-N

物化性质

• 沸点：
  655.7±55.0 °C(predicted)
• 密度：
  1.211±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-[1-(3,4-dimethoxyphenyl)-2-(2-methoxymethoxyphenyl)-2-oxoethyl]isoquinoline 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 20.5h， 生成 13-(3,4-Dimethoxy-phenyl)-10,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one
  参考文献：
  名称：

  Total Syntheses of Lamellarin D and H. The First Synthesis of Lamellarin-Class Marine Alkaloids

  摘要：

  Total syntheses of marine polyaromatic alkaloids, lamellarin D (1) and H (2), are described. The pentacyclic lamellarin ring system was constructed by B-ylide mediated pyrrole ring formation and subsequent lactonization of 4 obtained by an assembly of known benzylisoquinoline 5, benzoate 6 and ethyl bromoacetate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00287-1
• 作为产物：
  描述：

  水杨酸甲酯 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 6,7-dimethoxy-1-[1-(3,4-dimethoxyphenyl)-2-(2-methoxymethoxyphenyl)-2-oxoethyl]isoquinoline
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Study of Lamellarin Derivatives

  摘要：

  Ten derivatives (3-12) of marine alkaloid lamellarin D (1) were synthesized and evaluated for cytotoxicity against a HeLa cell line in an effort to examine their structure-activity relationships. It appeared that the hydroxyl groups at positions C-8 and C-20 of 1 were important structural requirements for cytotoxic activity, while the hydroxyl group at C-14 and the two methoxy groups at C-13 and C-21 were not necessary for the activity.

  DOI：

  10.1021/np0104525

文献信息

• Total Syntheses of Lamellarin D and H. The First Synthesis of Lamellarin-Class Marine Alkaloids
  作者：Fumito Ishibashi、Yuka Miyazaki、Masatomo Iwao

  DOI：10.1016/s0040-4020(97)00287-1

  日期：1997.4

  Total syntheses of marine polyaromatic alkaloids, lamellarin D (1) and H (2), are described. The pentacyclic lamellarin ring system was constructed by B-ylide mediated pyrrole ring formation and subsequent lactonization of 4 obtained by an assembly of known benzylisoquinoline 5, benzoate 6 and ethyl bromoacetate. (C) 1997 Elsevier Science Ltd.
• Synthesis and Structure−Activity Relationship Study of Lamellarin Derivatives
  作者：Fumito Ishibashi、Shinji Tanabe、Tatsuya Oda、Masatomo Iwao

  DOI：10.1021/np0104525

  日期：2002.4.1

  Ten derivatives (3-12) of marine alkaloid lamellarin D (1) were synthesized and evaluated for cytotoxicity against a HeLa cell line in an effort to examine their structure-activity relationships. It appeared that the hydroxyl groups at positions C-8 and C-20 of 1 were important structural requirements for cytotoxic activity, while the hydroxyl group at C-14 and the two methoxy groups at C-13 and C-21 were not necessary for the activity.