2-bromo-10,11-(methylenedioxy)aporphine | 119771-38-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 2-bromo-10,11-(methylenedioxy)aporphine
• 英文别名: (12R)-18-bromo-13-methyl-4,6-dioxa-13-azapentacyclo[10.7.1.02,10.03,7.016,20]icosa-1(19),2(10),3(7),8,16(20),17-hexaene
• CAS: 119771-38-9
• 化学式: C₁₈H₁₆BrNO₂
• 分子量: 358.235
• InChiKey: KWDXSELRNGQUPY-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-bromo-10,11-(methylenedioxy)aporphine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到2-bromoapomorphine hydrobromide
  参考文献：
  名称：

  2-Haloaporphines as potent dopamine agonists

  摘要：

  The synthesis of 2-amino- and 2-halo-substituted aporphines is described. The key step is the substitution of a hydroxy group in the 2-position with an amino group effected by a Smiles rearrangement reaction of the 2-methylpropanamide derivative 6. The affinity of the new compounds for the dopamine D-2 receptor in the anterior pituitary gland was evaluated. 2-Fluoroapomorphine was the most potent compound, being 1.5 times more potent than (-)-apomorphine. The structure-activity relationships are discussed in relation to a previously proposed receptor model.

  DOI：

  10.1021/jm00126a009
• 作为产物：
  描述：

  (R)(-)-2,10,11-trihydroxyaporphine hydrobromide 在 盐酸 、 六甲基磷酰三胺 、 ammonium hydroxide 、 sodium hydroxide 、 氯化亚砜 、 氢溴酸 、 sodium hydride 、 copper(I) bromide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 2-bromo-10,11-(methylenedioxy)aporphine
  参考文献：
  名称：

  2-Haloaporphines as potent dopamine agonists

  摘要：

  The synthesis of 2-amino- and 2-halo-substituted aporphines is described. The key step is the substitution of a hydroxy group in the 2-position with an amino group effected by a Smiles rearrangement reaction of the 2-methylpropanamide derivative 6. The affinity of the new compounds for the dopamine D-2 receptor in the anterior pituitary gland was evaluated. 2-Fluoroapomorphine was the most potent compound, being 1.5 times more potent than (-)-apomorphine. The structure-activity relationships are discussed in relation to a previously proposed receptor model.

  DOI：

  10.1021/jm00126a009

文献信息

• RAMSBY, STEN;NEUMEYER, JOHN L.;GRIGORIADIS, DIMITRI;SEEMAN, PHILIP, J. MED. CHEM., 32,(1989) N, C. 1198-1201
  作者：RAMSBY, STEN、NEUMEYER, JOHN L.、GRIGORIADIS, DIMITRI、SEEMAN, PHILIP

  DOI：——

  日期：——