N1-(7-bromo-4,5-dihydro-3H-1-benzazepin-2-yl)-N4,N9,N12-tri-tert-butoxycarbonylspermine | 1253528-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N1-(7-bromo-4,5-dihydro-3H-1-benzazepin-2-yl)-N4,N9,N12-tri-tert-butoxycarbonylspermine
• CAS: 1253528-41-4
• 化学式: C₃₅H₅₈BrN₅O₆
• 分子量: 724.779
• InChiKey: UMOHCZXKHYCKNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  121.8
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N1-(7-bromo-4,5-dihydro-3H-1-benzazepin-2-yl)-N4,N9,N12-tri-tert-butoxycarbonylspermine 在 盐酸 作用下， 以 乙醇 为溶剂， 以82%的产率得到N1-(7-bromo-4,5-dihydro-3H-1-benzazepin-2-yl)-spermine tetrahydrochloride
  参考文献：
  名称：

  Targeting the Polyamine Transport System with Benzazepine- and Azepine-Polyamine Conjugates

  摘要：

  The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.

  DOI：

  10.1021/jm1007648
• 作为产物：
  描述：

  2-甲基-2-丙基(3-氨基丙基)[4-({[(2-甲基-2-丙基)氧基]羰基}[3-({[(2-甲基-2-丙基)氧基]羰基}氨基)丙基]氨基)丁基]氨基甲酸酯 、 7-溴-1,3,4,5-四氢-2H-苯并[B]氮杂-2-硫酮 在 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以68%的产率得到N1-(7-bromo-4,5-dihydro-3H-1-benzazepin-2-yl)-N4,N9,N12-tri-tert-butoxycarbonylspermine
  参考文献：
  名称：

  Targeting the Polyamine Transport System with Benzazepine- and Azepine-Polyamine Conjugates

  摘要：

  The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.

  DOI：

  10.1021/jm1007648