(S)-10,11-dimethoxy-N-allylnoraporphine | 736107-44-1

• 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: (S)-10,11-dimethoxy-N-allylnoraporphine
• 英文别名: (6aS)-10,11-dimethoxy-6-prop-2-enyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• CAS: 736107-44-1
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: IZVFWZGHFVOEPH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-N-benzylnorapocodeine hydrochloride 在 palladium on activated charcoal 盐酸 、 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 85.0h， 生成 (S)-10,11-dimethoxy-N-allylnoraporphine
  参考文献：
  名称：

  (R)- and (S)-enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue

  摘要：

  The R-(-)- and S-(+)-enantiomers of 11-hydroxy-N-allyl (4), and 10,11-dihydroxy-N-allyl (3) congeners of 11-hydroxy-N-n-propylnoraporphine (11-OH-NPa, 2) or N-n-propylnorapomorphine (NPA, 1) were synthesized. Binding affinity of these compounds at dopamine (DA) receptor sites was evaluated with a membrane preparation of corpus striatum from rat brain. The R/S enantiomeric receptor affinity ratio was enhanced by allylic substitution of 3 and 4 and their R isomers had high DA receptor affinity similar to that of the N-n-propyl congeners. These N-allylaporphines are proposed as useful precursors to the preparation of their tritiated N-n-propyl enantiomers.

  DOI：

  10.1021/jm00105a005