5-(2-dimethylaminoethyl)-9-(2-dimethylaminoethylamino)-2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-one | 1149338-46-4

• 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-(2-dimethylaminoethyl)-9-(2-dimethylaminoethylamino)-2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-one
• 英文别名: 21-[2-(Dimethylamino)ethyl]-16-[2-(dimethylamino)ethylamino]-5,7-dioxa-11,21-diazapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-one
• CAS: 1149338-46-4
• 化学式: C₂₅H₂₉N₅O₃
• 分子量: 447.537
• InChiKey: IRCMQKKHKYUNMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  二甲氨基乙醛缩二乙醇 、 9-amino-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxybenzo[c,h]-1,6-naphthyridin-6-one 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以32%的产率得到5-(2-dimethylaminoethyl)-9-(2-dimethylaminoethylamino)-2,3-methylenedioxy-5H-dibenzo[c,h][1,6]naphthyridin-6-one
  参考文献：
  名称：

  Cytotoxicity and TOP1-targeting activity of 8- and 9-amino derivatives of 5-butyl- and 5-(2-N,N-dimethylamino)ethyl-5H-dibenzo[c,h][1,6]naphthyridin-6-ones

  摘要：

  Studies on substituted 5H-dibenzo[c,h][1,6]naphthyridin-6-ones and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones have demonstrated that hydrophilic substituents at the 2-position of an ethyl group at the 5- and 6-positions, respectively, can enhance biological activity. The compatibility of such hydrophilic groups at other sites with either TOP1-targeting activity or potent cytotoxic activity has not been explored. The present study examines the influence on biological activity of either a 2-(N,N-dimethylamino)ethyl or a N,N-dimethylacetamide derivative of 8- or 9-amino-5H-dibenzo[c,h]naphthyridin-6-ones that have a 5-butyl- or 5-[2-(N,N-dimethylamino)ethyl]-substituent. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.048

文献信息

• Cytotoxicity and TOP1-targeting activity of 8- and 9-amino derivatives of 5-butyl- and 5-(2-N,N-dimethylamino)ethyl-5H-dibenzo[c,h][1,6]naphthyridin-6-ones
  作者：Lisa Sharma、Yuan-Chin Tsai、Angela A. Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/j.ejmech.2008.09.048

  日期：2009.4

  Studies on substituted 5H-dibenzo[c,h][1,6]naphthyridin-6-ones and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones have demonstrated that hydrophilic substituents at the 2-position of an ethyl group at the 5- and 6-positions, respectively, can enhance biological activity. The compatibility of such hydrophilic groups at other sites with either TOP1-targeting activity or potent cytotoxic activity has not been explored. The present study examines the influence on biological activity of either a 2-(N,N-dimethylamino)ethyl or a N,N-dimethylacetamide derivative of 8- or 9-amino-5H-dibenzo[c,h]naphthyridin-6-ones that have a 5-butyl- or 5-[2-(N,N-dimethylamino)ethyl]-substituent. (C) 2008 Elsevier Masson SAS. All rights reserved.