N-(quinolin-4-yl)-N-[2-(N,N-dimethylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide | 738622-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(quinolin-4-yl)-N-[2-(N,N-dimethylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide
• 英文别名: N-(quinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodo-4,5-dimethoxybenzamide
• CAS: 738622-65-6
• 化学式: C₂₂H₂₄IN₃O₃
• 分子量: 505.355
• InChiKey: QSYPHQLJDGOSJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(quinolin-4-yl)-N-[2-(N,N-dimethylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide 在 palladium diacetate 、 三(邻甲基苯基)磷 、 silver carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 25.0h， 以42%的产率得到8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-5H-dibenzo[c,h][1,6]naphthyridin-6-one
  参考文献：
  名称：

  [EN] NITRO AND AMINO SUBSTITUTED DIBENZONAPHTHYRIDINES AS TOPOISOMERASE AGENTS
  [FR] AGENTS TOPOISOMERASE NITRO ET AMINO SUBSTITUES

  摘要：

  公开号：

  WO2004014906A3
• 作为产物：
  描述：

  4-氯喹啉 在 三乙胺 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 N-(quinolin-4-yl)-N-[2-(N,N-dimethylamino)ethyl]-2-iodo-4,5-dimethoxybenzamide
  参考文献：
  名称：

  Nitro and amino substitution within the A-ring of 5H-8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: influence on topoisomerase I-targeting activity and cytotoxicity

  摘要：

  Recently, 5H-8 9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c,h][1,6]naphthyridin-6-one, 1, was identified as a TOP1-targeting agent with pronounced antitumor activity. In the present study, the effect on activity of substituting, a single nitro or amino group in the A-ring in lieu of the methylenedioxy moiety of 1 was evaluated. The presence of either a nitro or amino substituent at the 4-position had a pronounced adverse affect on both TOP1-targeting activity and cytotoxicity. To a lesser extent, derivatives with a nitro or amino substituent at the 1-position were also less active than 1. Replacement of the methylenedioxy moiety of 1 with either a nitro or amino substituent at either the 2- and 3-position did result in analogues with potent TOP1-targeting activity and cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.076