2-(8-Thiazolidin-3-yl-octyl)-isoindole-1,3-dione | 187977-48-6

• 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: 2-(8-Thiazolidin-3-yl-octyl)-isoindole-1,3-dione
• 英文别名: 2-[8-(1,3-Thiazolidin-3-yl)octyl]isoindole-1,3-dione
• CAS: 187977-48-6
• 化学式: C₁₉H₂₆N₂O₂S
• 分子量: 346.494
• InChiKey: SEDGFPWMDXRPFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(8-Thiazolidin-3-yl-octyl)-isoindole-1,3-dione 在 甲胺 作用下， 以 乙醇 为溶剂， 以78%的产率得到3-(8-aminooctyl)-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
• 作为产物：
  描述：

  1,8-bis(p-toluenesulfonyloxy)octane 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.0h， 生成 2-(8-Thiazolidin-3-yl-octyl)-isoindole-1,3-dione
  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

• 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.