3-(12-aminododecyl)-1,3-thiazolidine | 115483-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(12-aminododecyl)-1,3-thiazolidine
• 英文别名: 12-(1,3-Thiazolidin-3-yl)dodecan-1-amine
• CAS: 115483-37-9
• 化学式: C₁₅H₃₂N₂S
• 分子量: 272.498
• InChiKey: UMSSZRJJRYOEIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(12-aminododecyl)-1,3-thiazolidine 在 碘 、 三乙胺 、 potassium iodide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 N,N''-(dithiodi-2,1-ethanediyl)-N,N''-dimethylbis(1,12-dodecanediamine)
  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：

  12-(1,3-Thiazolidin-3-yl)dodecyl 4-methylbenzenesulfonate 在 甲胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 3-(12-aminododecyl)-1,3-thiazolidine
  参考文献：
  名称：

  Synthesis and α1-antagonist activity of new prazosin- and benextramine-related tetraamine disulfides

  摘要：

  Tetraamine disulfides 1-10 were designed by combining the structural features of benextramine, an irreversible alpha(1)/alpha(2)-adrenoceptor antagonist, and prazosin, a selective competitive alpha(1)-antagonist. Their biological profile was assessed by functional and binding assays. In rat vas deferens functional experiments, tetraamine disulfides 1-10 displayed a marked selectivity at alpha(1)-adrenoceptors. Furthermore, they acted as competitive antagonists at alpha(1)-adrenoceptors and weak noncompetitive (irreversible) antagonists at alpha(2)-adrenoceptors. In binding assays, performed at alpha(1)-adrenoceptors of rat liver (alpha 1B) and submaxillary gland (alpha(1A), compound 5 showed an 11-fold selectivity for alpha(1B)-adrenoceptors in contrast to both prazosin and benextramine, which were not selective or selective for the alpha(1A)-subtype respectively.

  DOI：

  10.1016/s0223-5234(97)84357-7

文献信息

• Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on .alpha.-adrenoreceptor blocking activity
  作者：Wilma Quaglia、Livio Brasili、Gloria Cristalli、Dario Giardina、Maria T. Picchio、Carlo Melchiorre

  DOI：10.1021/jm00117a030

  日期：1988.9

  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.
• Synthesis and α1-antagonist activity of new prazosin- and benextramine-related tetraamine disulfides
  作者：D Giardinà、M Crucianelli、U Gulini、G Marucci、C Melchiorre、S Spampinato

  DOI：10.1016/s0223-5234(97)84357-7

  日期：1997.1

  Tetraamine disulfides 1-10 were designed by combining the structural features of benextramine, an irreversible alpha(1)/alpha(2)-adrenoceptor antagonist, and prazosin, a selective competitive alpha(1)-antagonist. Their biological profile was assessed by functional and binding assays. In rat vas deferens functional experiments, tetraamine disulfides 1-10 displayed a marked selectivity at alpha(1)-adrenoceptors. Furthermore, they acted as competitive antagonists at alpha(1)-adrenoceptors and weak noncompetitive (irreversible) antagonists at alpha(2)-adrenoceptors. In binding assays, performed at alpha(1)-adrenoceptors of rat liver (alpha 1B) and submaxillary gland (alpha(1A), compound 5 showed an 11-fold selectivity for alpha(1B)-adrenoceptors in contrast to both prazosin and benextramine, which were not selective or selective for the alpha(1A)-subtype respectively.