(S)-(+)-11-hydroxy-N-n-propylnoraporphine | 114033-64-6

• 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)-(+)-11-hydroxy-N-n-propylnoraporphine
• 英文别名: (+)-11-Hydroxy-N-propylnoraporphine；S(+)11-hydroxy-N-propylnoraporphine；6-Propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol；(6aS)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
• CAS: 114033-64-6
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: WZJSIHGOLMMBAL-INIZCTEOSA-N

物化性质

• 沸点：
  454.7±33.0 °C(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-苯乙基异氰酸酯 、 (S)-(+)-11-hydroxy-N-n-propylnoraporphine 在 三乙胺 作用下， 反应 5.0h， 生成 ((S)-1-Phenyl-ethyl)-carbamic acid (S)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl ester
  参考文献：
  名称：

  Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine

  摘要：

  The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.

  DOI：

  10.1021/jm00402a024
• 作为产物：
  描述：

  (S)-(+)-11-methoxy-N-n-propylnoraporphine hydrochloride 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 (S)-(+)-11-hydroxy-N-n-propylnoraporphine
  参考文献：
  名称：

  Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine

  摘要：

  The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.

  DOI：

  10.1021/jm00402a024

文献信息

• NEUMEYER, JOHN L.;BALDESSARINI, ROSS J.
  作者：NEUMEYER, JOHN L.、BALDESSARINI, ROSS J.

  DOI：——

  日期：——
• US4687773A
  申请人：——

  公开号：US4687773A

  公开（公告）日：1987-08-18
• Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine
  作者：Yigong Gao、Rushi Zong、Alexander Campbell、Nora S. Kula、Ross J. Baldessarini、John L. Neumeyer

  DOI：10.1021/jm00402a024

  日期：1988.7

  The R-(-) and S-(+) enantiomers of 11-hydroxy-N-n-propylnoraporphine, (R)-3 and (S)-3, were synthesized in six steps from 1-(3-methoxy-2-nitrobenzyl)isoquinoline. Neuropharmacological evaluation of the R and S isomers (by affinity to dopamine receptor sites in rat brain tissues, induction of stereotyped behavior, and interaction with motor arousal induced by (R)-apomorphine in the rat) indicated that, similar to the 10,11-dihydroxy congener 2, both enantiomers can bind to dopamine receptors but that only (R)-3 activates them, whereas (S)-3 shows activity as a dopaminergic antagonist.