N-(2-(dimethylamino)ethyl)-9-(6-(5-(dimethylamino)naphthalene-1-sulfonamido)hexylamino)acridine-3-carboxamide | 1260084-09-0

• 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: N-(2-(dimethylamino)ethyl)-9-(6-(5-(dimethylamino)naphthalene-1-sulfonamido)hexylamino)acridine-3-carboxamide
• CAS: 1260084-09-0
• 化学式: C₃₆H₄₄N₆O₃S
• 分子量: 640.85
• InChiKey: GZEDZZRBSCSMJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106.67
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(2-(dimethylamino)ethyl)-9-(6-(5-(dimethylamino)naphthalene-1-sulfonamido)hexylamino)acridine-3-carboxamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以85%的产率得到N-(2-(dimethylamino)ethyl)-9-(6-(5-(dimethylamino)naphthalene-1-sulfonamido)hexylamino)acridine-3-carboxamide trihydrochloride
  参考文献：
  名称：

  Design and synthesis of threading intercalators to target DNA

  摘要：

  Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based upon the well studied acridine-3- or 4-carboxamides. Cellular uptake of the parent acridine is rapid and it can be visualized in the nucleus of cells. Both the parent compounds and their conjugates maintain antitumor activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.128
• 作为产物：
  描述：

  9-((6-aminohexylamino)-N-(2-dimethylamino)ethyl)acridine-3-carboxamide hydrochloride 、 丹酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以40%的产率得到N-(2-(dimethylamino)ethyl)-9-(6-(5-(dimethylamino)naphthalene-1-sulfonamido)hexylamino)acridine-3-carboxamide
  参考文献：
  名称：

  Design and synthesis of threading intercalators to target DNA

  摘要：

  Threading intercalators are high affinity DNA binding agents that bind by inserting a chromophore into the duplex and locating one group in each groove. The first threading intercalators that can be conjugated to acids, sulfonic acids and peptides to target them to duplex DNA are described, based upon the well studied acridine-3- or 4-carboxamides. Cellular uptake of the parent acridine is rapid and it can be visualized in the nucleus of cells. Both the parent compounds and their conjugates maintain antitumor activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.128