8α-[(2-mercaptopropionyl)amino]-6-methylergoline | 178443-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8α-[(2-mercaptopropionyl)amino]-6-methylergoline
• CAS: 178443-58-8
• 化学式: C₁₈H₂₃N₃OS
• 分子量: 329.466
• InChiKey: VTVBWAIDDINNOT-YNXLTHNQSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  587.9±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.13
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8α-[(2-mercaptopropionyl)amino]-6-methylergoline 、 碘甲烷 以 甲醇 为溶剂， 以23.5 mg的产率得到8α-[[2-(methylsulfanyl)propionyl]amino]-6-methylergoline
  参考文献：
  名称：

  Tc and Re Chelates of 8α-Amino-6-methyl-ergoline: Synthesis and Affinity to the Dopamine D2 Receptor

  摘要：

  The influence of structural changes at the 8alpha-amino position of 8alpha-amino-6-methyl-ergoline on the lipophilicity and affinity to the D-2 receptor was studied. 8a-amino-6-methyl-ergoline (1) was converted into the derivatives (2a-f) by mercaptoacetylation of the amino group to make it possible to prepare the rhenium and technetium complexes (3, 4a,b). Binding tests on cloned human dopamine D2 receptors show that the affinities of the coordination compounds (IC50 values between 50 and 240 nM) are less than those of the derivatives 2a-f (IC50 = 3-50 nM) but more than those of the parent compound 1. Biodistribution studies of the Tc complexes 4a,b performed on Wistar rats show a slow blood clearance with substantial accumulation and retention in the liver and kidneys and low brain uptake. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00214-6
• 作为产物：
  描述：

  8α-[[2-(benzoylsulfanyl)propionyl]amino]-6-methylergoline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以47%的产率得到8α-[(2-mercaptopropionyl)amino]-6-methylergoline
  参考文献：
  名称：

  Tc and Re Chelates of 8α-Amino-6-methyl-ergoline: Synthesis and Affinity to the Dopamine D2 Receptor

  摘要：

  The influence of structural changes at the 8alpha-amino position of 8alpha-amino-6-methyl-ergoline on the lipophilicity and affinity to the D-2 receptor was studied. 8a-amino-6-methyl-ergoline (1) was converted into the derivatives (2a-f) by mercaptoacetylation of the amino group to make it possible to prepare the rhenium and technetium complexes (3, 4a,b). Binding tests on cloned human dopamine D2 receptors show that the affinities of the coordination compounds (IC50 values between 50 and 240 nM) are less than those of the derivatives 2a-f (IC50 = 3-50 nM) but more than those of the parent compound 1. Biodistribution studies of the Tc complexes 4a,b performed on Wistar rats show a slow blood clearance with substantial accumulation and retention in the liver and kidneys and low brain uptake. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00214-6