3,11-bis(benzyloxy)-2,12-dimethoxy-14-(3-methoxyphenyl)-6H[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline-6-one | 422566-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,11-bis(benzyloxy)-2,12-dimethoxy-14-(3-methoxyphenyl)-6H[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline-6-one
• 英文别名: 8,16-Dimethoxy-12-(3-methoxyphenyl)-7,17-bis(phenylmethoxy)-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-3-one
• CAS: 422566-57-2
• 化学式: C₄₂H₃₃NO₇
• 分子量: 663.727
• InChiKey: AMVQNTNPCZSEAL-UHFFFAOYSA-N

物化性质

• 熔点：
  270-271 °C
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,11-bis(benzyloxy)-2,12-dimethoxy-14-(3-methoxyphenyl)-6H[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline-6-one 在 palladium hydroxide - carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 8.0h， 以72%的产率得到3,10-Dihydroxy-2,11-dimethoxy-13-(3-methoxy-phenyl)-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one
  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
• 作为产物：
  描述：

  Methyl 5-methoxy-2-(methoxymethoxy)-4-phenylmethoxybenzoate 在 盐酸 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 26.5h， 生成 3,11-bis(benzyloxy)-2,12-dimethoxy-14-(3-methoxyphenyl)-6H[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline-6-one
  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

• 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.