5-[(thiophen-2-yimethyl)-amino]-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1098129-21-5

• 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: 5-[(thiophen-2-yimethyl)-amino]-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[2-(Dimethylamino)ethyl]-5-(thiophen-2-ylmethylamino)benzo[de]isoquinoline-1,3-dione
• CAS: 1098129-21-5
• 化学式: C₂₁H₂₁N₃O₂S
• 分子量: 379.483
• InChiKey: YYJHDZAKITVAOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩甲胺 、 N-[(2-dimethylamino)ethyl]-3-bromo-1,8-naphthalimide 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以31%的产率得到5-[(thiophen-2-yimethyl)-amino]-2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis of new amonafide analogues via coupling reaction and their cytotoxic evaluation and DNA-binding studies

  摘要：

  A series of 5-alkylamino substituted amonafide analogues were synthesized from naphthalic anhydride by three steps including bromization, amination and CuI/proline catalyzed coupling reaction. The CuI/L-proline catalyzed coupling reaction was first applied to the naphthalimide system. These new amonafide analogues showed potential anticancer activities against HeLa and P388D1 cell lines in vitro, and 4a, 4b, and 4h exhibited better activity than amonafide against HeLa cell under the same experimental conditions. More importantly, the new analogues could avoid the side effect of amonafide due to their structure, in which lacks a primary amine at the 5 position. Moreover, the DNA-binding of the analogues was also investigated. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.11.053

文献信息

• Synthesis of new amonafide analogues via coupling reaction and their cytotoxic evaluation and DNA-binding studies
  作者：Lijuan Xie、Yufang Xu、Fang Wang、Jianwen Liu、Xuhong Qian、Jingnan Cui

  DOI：10.1016/j.bmc.2008.11.053

  日期：2009.1

  A series of 5-alkylamino substituted amonafide analogues were synthesized from naphthalic anhydride by three steps including bromization, amination and CuI/proline catalyzed coupling reaction. The CuI/L-proline catalyzed coupling reaction was first applied to the naphthalimide system. These new amonafide analogues showed potential anticancer activities against HeLa and P388D1 cell lines in vitro, and 4a, 4b, and 4h exhibited better activity than amonafide against HeLa cell under the same experimental conditions. More importantly, the new analogues could avoid the side effect of amonafide due to their structure, in which lacks a primary amine at the 5 position. Moreover, the DNA-binding of the analogues was also investigated. (C) 2009 Published by Elsevier Ltd.