N-[3-(imidazol-1-yl)propyl](4-dimethylamino)-1,8-naphthalimide | 1396227-77-2

• 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: N-[3-(imidazol-1-yl)propyl](4-dimethylamino)-1,8-naphthalimide
• 英文别名: 6-(Dimethylamino)-2-(3-imidazol-1-ylpropyl)benzo[de]isoquinoline-1,3-dione；6-(dimethylamino)-2-(3-imidazol-1-ylpropyl)benzo[de]isoquinoline-1,3-dione
• CAS: 1396227-77-2
• 化学式: C₂₀H₂₀N₄O₂
• 分子量: 348.404
• InChiKey: QNCNQFQUCSNFSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis[dichlorido(η6-toluene)ruthenium(II)] 、 N-[3-(imidazol-1-yl)propyl](4-dimethylamino)-1,8-naphthalimide 以 二氯甲烷 为溶剂， 反应 18.0h， 以84%的产率得到{dichloro(η⁶-toluene)(N-[3-(imidazol-1-yl)propyl](4-dimethylamino)-1,8-naphthalimide)ruthenium(II)}
  参考文献：
  名称：

  Naphthalimide-Tagged Ruthenium–Arene Anticancer Complexes: Combining Coordination with Intercalation

  摘要：

  Ruthenium(II) arene compounds have been modified with the naphthalimide group, tethered via the arene ligand, i.e. {dichloro[eta(6)-N-(phenylalkyl)(4-dimethylamino)-1,8-naphthalimide](pta)ruthenium(II)} (alkyl = methyl, ethyl, propyl, pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]-decane), or via an imidazole group, i.e. {dichloro(eta(6)-arene)-(N-[3-(imidazol-1-yl)propyl]-1,8-naphthalimide)ruthenium(II)} (II)} (arene = p-cymene, toluene). All the compounds are reasonably cytotoxic (ca. 2-49 mu M) toward cancer cells, and the arene-linked compounds also display selectivity in that they are less cytotoxic toward model healthy cells. Mechanistic studies show that the ruthenium center does not readily react with DNA but preferentially binds to proteins. In contrast, the naphthalimide group is a strong DNA intercalator, and combined, the complexes might be expected to simultaneously cross-link DNA and proteins.

  DOI：

  10.1021/om3007079
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 copper(ll) sulfate pentahydrate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 N-[3-(imidazol-1-yl)propyl](4-dimethylamino)-1,8-naphthalimide
  参考文献：
  名称：

  Naphthalimide-Tagged Ruthenium–Arene Anticancer Complexes: Combining Coordination with Intercalation

  摘要：

  Ruthenium(II) arene compounds have been modified with the naphthalimide group, tethered via the arene ligand, i.e. {dichloro[eta(6)-N-(phenylalkyl)(4-dimethylamino)-1,8-naphthalimide](pta)ruthenium(II)} (alkyl = methyl, ethyl, propyl, pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]-decane), or via an imidazole group, i.e. {dichloro(eta(6)-arene)-(N-[3-(imidazol-1-yl)propyl]-1,8-naphthalimide)ruthenium(II)} (II)} (arene = p-cymene, toluene). All the compounds are reasonably cytotoxic (ca. 2-49 mu M) toward cancer cells, and the arene-linked compounds also display selectivity in that they are less cytotoxic toward model healthy cells. Mechanistic studies show that the ruthenium center does not readily react with DNA but preferentially binds to proteins. In contrast, the naphthalimide group is a strong DNA intercalator, and combined, the complexes might be expected to simultaneously cross-link DNA and proteins.

  DOI：

  10.1021/om3007079

文献信息

• Naphthalimide-Tagged Ruthenium–Arene Anticancer Complexes: Combining Coordination with Intercalation
  作者：Kelly J. Kilpin、Catherine M. Clavel、Fabio Edafe、Paul J. Dyson

  DOI：10.1021/om3007079

  日期：2012.10.22

  Ruthenium(II) arene compounds have been modified with the naphthalimide group, tethered via the arene ligand, i.e. dichloro[eta(6)-N-(phenylalkyl)(4-dimethylamino)-1,8-naphthalimide](pta)ruthenium(II)} (alkyl = methyl, ethyl, propyl, pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]-decane), or via an imidazole group, i.e. dichloro(eta(6)-arene)-(N-[3-(imidazol-1-yl)propyl]-1,8-naphthalimide)ruthenium(II)} (II)} (arene = p-cymene, toluene). All the compounds are reasonably cytotoxic (ca. 2-49 mu M) toward cancer cells, and the arene-linked compounds also display selectivity in that they are less cytotoxic toward model healthy cells. Mechanistic studies show that the ruthenium center does not readily react with DNA but preferentially binds to proteins. In contrast, the naphthalimide group is a strong DNA intercalator, and combined, the complexes might be expected to simultaneously cross-link DNA and proteins.