(S)-(+)-11-methoxy-N-n-propylnoraporphine hydrochloride | 113678-77-6

• 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-methoxy-N-n-propylnoraporphine hydrochloride
• 英文别名: 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-11-methoxy-6-propyl-, hydrochloride, (S)-(9CI)；(6aS)-11-methoxy-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline;hydrochloride
• CAS: 113678-77-6
• 化学式: C₂₀H₂₃NO*ClH
• 分子量: 329.87
• InChiKey: FDSPMFUNDIUYMT-LMOVPXPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (S)-6-Allyl-11-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (S)-(+)-11-methoxy-N-n-propylnoraporphine hydrochloride
  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

文献信息

• NEUMEYER, JOHN L.;GAO, YIGONG;KULA, NORA S.;BALDESSARINI, ROSS J., J. MED. CHEM., 34,(1991) N, C. 24-28
  作者：NEUMEYER, JOHN L.、GAO, YIGONG、KULA, NORA S.、BALDESSARINI, ROSS J.

  DOI：——

  日期：——
• GAO, YIGONG;ZONG, RUSHI;CAMPBELL, ALEXANDER;KULA, NORA S.;BALDESSARINI, R+, J. MED. CHEM., 31,(1988) N 7, 1392-1396
  作者：GAO, YIGONG、ZONG, RUSHI、CAMPBELL, ALEXANDER、KULA, NORA S.、BALDESSARINI, R+

  DOI：——

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

  DOI：——

  日期：——
• (R)- and (S)-enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue
  作者：John L. Neumeyer、Nora S. Kula、Ross J. Baldessarini、Yigong Gao

  DOI：10.1021/jm00105a005

  日期：1991.1

  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.
• 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.