2-<(aminocarbonyl)dimethylmethoxy>-10,11-(methylenedioxy)aporphine | 119771-34-5

• 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-<(aminocarbonyl)dimethylmethoxy>-10,11-(methylenedioxy)aporphine
• 英文别名: 2-[(aminocarbonyl)dimethylmethoxy]-10,11-(methylenedioxy)aporphine；2-methyl-2-[[(12R)-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-hexaen-18-yl]oxy]propanamide
• CAS: 119771-34-5
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: FCVBAWNSYBSBDG-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.02
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-<(aminocarbonyl)dimethylmethoxy>-10,11-(methylenedioxy)aporphine 在 盐酸 、 六甲基磷酰三胺 、 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-Fluoroapomorphine 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 ammonium hydroxide 、 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 2-<(aminocarbonyl)dimethylmethoxy>-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：——