3,4-bis(7',8'-dimethoxyquinolin-5'-yl)pyrrole | 460991-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,4-bis(7',8'-dimethoxyquinolin-5'-yl)pyrrole
• 英文别名: 5-[4-(7,8-dimethoxyquinolin-5-yl)-1H-pyrrol-3-yl]-7,8-dimethoxyquinoline
• CAS: 460991-91-7
• 化学式: C₂₆H₂₃N₃O₄
• 分子量: 441.486
• InChiKey: CYPHPASMPIFHLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-Methylazecan-1-yl)propyl trifluoromethanesulfonate 、 3,4-bis(7',8'-dimethoxyquinolin-5'-yl)pyrrole 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 15.1h， 以87%的产率得到
  参考文献：
  名称：

  Rapid and convergent assembly of the polycyclic framework assigned to the cytotoxic marine alkaloid halitulin

  摘要：

  化合物 3 是结构 1 的四-O-甲基醚衍生物，属于具有细胞毒性的海洋生物碱 halitulin，由现成的结构单元 5、6 和 11 以聚合的方式组装而成。

  DOI：

  10.1039/b111401h
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 在 sodium hydroxide 、 萘 、 四丁基氟化铵 、 四丁基碘化铵 、 lithium 、 potassium carbonate 、 苯基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 3,4-bis(7',8'-dimethoxyquinolin-5'-yl)pyrrole
  参考文献：
  名称：

  Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

  摘要：

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00637-3

文献信息

• Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core
  作者：Alois Fürstner、Helga Krause、Oliver R Thiel

  DOI：10.1016/s0040-4020(02)00637-3

  日期：2002.8

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Rapid and convergent assembly of the polycyclic framework assigned to the cytotoxic marine alkaloid halitulin
  作者：Martin G. Banwell、Andrew M. Bray、Alison J. Edwards、David J. Wong

  DOI：10.1039/b111401h

  日期：2002.5.23

  Compound 3, representing the tetra-O-methyl ether derivative of structure, 1, assigned to the cytotoxic marine alkaloid halitulin, has been assembled in a convergent manner from the readily available building blocks 5, 6 and 11.

  化合物 3 是结构 1 的四-O-甲基醚衍生物，属于具有细胞毒性的海洋生物碱 halitulin，由现成的结构单元 5、6 和 11 以聚合的方式组装而成。