N-<11-(1,3-thiazolidin-3-yl)undecyl>phthalimide | 115483-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-<11-(1,3-thiazolidin-3-yl)undecyl>phthalimide
• 英文别名: 2-[11-(1,3-thiazolidin-3-yl)undecyl]isoindole-1,3-dione
• CAS: 115483-34-6
• 化学式: C₂₂H₃₂N₂O₂S
• 分子量: 388.574
• InChiKey: JYQLWAHRMSWJGF-UHFFFAOYSA-N

物化性质

• 沸点：
  516.1±35.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-<11-(1,3-thiazolidin-3-yl)undecyl>phthalimide 在 sodium hydroxide 、 碘 、 一水合肼 、 potassium iodide 作用下， 反应 24.0h， 生成 N-(2-Methoxy-benzyl)-N'-(2-{2-[11-(2-methoxy-benzylamino)-undecylamino]-ethyldisulfanyl}-ethyl)-undecane-1,11-diamine
  参考文献：
  名称：

  Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on .alpha.-adrenoreceptor blocking activity

  摘要：

  Several N'-substituted N,N''-(dithiodi-2,1-ethanediyl)bis(1, omega-alkanediamines) were prepared and evaluated for their blocking activity on alpha-adrenoreceptors in the isolated rat vas deferens and human blood platelets. The results were compared with those obtained for benextramine (N,N''-(dithiodi-2,1-ethanediyl)bis[N'-[(2-methoxyphenyl)-methyl]- 1 ,6- hexanediamine], 10). Bendotramine (N,N''-(dithiodi-2,1-ethanediyl)bis[N'-[(2-methoxyphenyl)- methyl]-1,12-dodecanediamine], 16) proved to be as active as 10 on alpha 1-adrenoreceptors, showing that optimum activity is associated with two carbon chain lengths separating inner from outer nitrogens of tetraamine disulfides. On the other hand, 16 had no activity up to 20 microM at alpha 2-adrenoreceptors. The optimum activity at this receptor subtype was associated with a six to eight carbon chain (10-12). Furthermore, 10 proved to be more selective toward alpha 2-adrenoreceptors whereas 16 was a selective alpha 1-antagonist. The tetraamine disulfides were shown also to be potent inhibitors of human platelet aggregation induced by ADP or epinephrine. The potency increased with the carbon chain length. However, the results on platelets did not parallel those found in the rat vas deferens, indicating that differences exist between the alpha-adrenoreceptor subtypes investigated. In conclusion, 10 may be a useful tool in characterizing alpha 2-adrenoreceptors whereas 16 might help in investigating alpha 1-adrenoreceptors.

  DOI：

  10.1021/jm00117a030
• 作为产物：
  描述：

  四氢噻唑 、 N-(11-bromoundecyl)phthalimide 以 乙醇 为溶剂， 反应 40.0h， 以1.25 g的产率得到N-<11-(1,3-thiazolidin-3-yl)undecyl>phthalimide
  参考文献：
  名称：

  Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on .alpha.-adrenoreceptor blocking activity

  摘要：

  Several N'-substituted N,N''-(dithiodi-2,1-ethanediyl)bis(1, omega-alkanediamines) were prepared and evaluated for their blocking activity on alpha-adrenoreceptors in the isolated rat vas deferens and human blood platelets. The results were compared with those obtained for benextramine (N,N''-(dithiodi-2,1-ethanediyl)bis[N'-[(2-methoxyphenyl)-methyl]- 1 ,6- hexanediamine], 10). Bendotramine (N,N''-(dithiodi-2,1-ethanediyl)bis[N'-[(2-methoxyphenyl)- methyl]-1,12-dodecanediamine], 16) proved to be as active as 10 on alpha 1-adrenoreceptors, showing that optimum activity is associated with two carbon chain lengths separating inner from outer nitrogens of tetraamine disulfides. On the other hand, 16 had no activity up to 20 microM at alpha 2-adrenoreceptors. The optimum activity at this receptor subtype was associated with a six to eight carbon chain (10-12). Furthermore, 10 proved to be more selective toward alpha 2-adrenoreceptors whereas 16 was a selective alpha 1-antagonist. The tetraamine disulfides were shown also to be potent inhibitors of human platelet aggregation induced by ADP or epinephrine. The potency increased with the carbon chain length. However, the results on platelets did not parallel those found in the rat vas deferens, indicating that differences exist between the alpha-adrenoreceptor subtypes investigated. In conclusion, 10 may be a useful tool in characterizing alpha 2-adrenoreceptors whereas 16 might help in investigating alpha 1-adrenoreceptors.

  DOI：

  10.1021/jm00117a030

文献信息

• QUAGLIA, WILMA;BRASILI, LIVIO;CRISTALLI, GLORIA;GIARDINA, DARIO;PICCHIO, +, J. MED. CHEM., 31,(1988) N 9, C. 1861-1866
  作者：QUAGLIA, WILMA、BRASILI, LIVIO、CRISTALLI, GLORIA、GIARDINA, DARIO、PICCHIO, +

  DOI：——

  日期：——