(+)-4-[(αR)-α-((2S,5R)-4-(3-phenyl)-propyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-4-[(αR)-α-((2S,5R)-4-(3-phenyl)-propyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide
• 英文别名: 4-[(R)-[(2S,5R)-2,5-dimethyl-4-(3-phenylpropyl)piperazin-1-yl]-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide
• 化学式: C₃₄H₄₅N₃O₂
• 分子量: 527.75
• InChiKey: FBWUFLYPVWIVGR-OEYLZLLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+)-4-[(ΑR)-Α-((2S,5R)-4-烯丙基-2,5-二甲基-1-哌嗪基)-3-甲氧基苄基]-N,N-二乙基苯酰胺 在 10percent Pd/C 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (+)-4-[(αR)-α-((2S,5R)-4-(3-phenyl)-propyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide
  参考文献：
  名称：

  Probes for Narcotic Receptor-Mediated Phenomena. 27. Synthesis and Pharmacological Evaluation of Selective δ-Opioid Receptor Agonists from 4-[(αR)-α-(2S,5R)-4-Substituted-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]- N,N-diethylbenzamides and Their Enantiomers

  摘要：

  Potent, selective, and efficacious delta-opioid receptor agonists such as (+)-4-[(alpha R)-alpha-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide [SNC80, (+)-2] have been found to be useful tools for exploring the structural requirements which are necessary for ligands which interact with the delta-receptor. To determine the necessity for the 4-allyl moiety in (+)-2, this substituent was replaced with a variety of 4-alkyl, 4-arylalkyl, and 4-alkenyl substituents. The corresponding enantiomers of these compounds were also synthesized. The binding affinities for the mu-, delta-, and kappa-opioid receptors and efficacies in the functional GTP gamma S binding assay were determined for the (+)-2 related compounds and their enantiomers. The 4-crotyl analogue was found to have similar delta-receptor affinity and efficacy as (+)-2, but the 4-cyclopropylmethyl analogue, in the functional assay, appeared to be a partial agonist with little antagonist activity.

  DOI：

  10.1021/jm0001222

文献信息

• Probes for Narcotic Receptor-Mediated Phenomena. 27. Synthesis and Pharmacological Evaluation of Selective δ-Opioid Receptor Agonists from 4-[(α<i>R</i>)-α-(2<i>S</i>,5<i>R</i>)-4-Substituted-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]- <i>N</i>,<i>N</i>-diethylbenzamides and Their Enantiomers
  作者：M. Scott Furness、Xiaoyan Zhang、Andrew Coop、Arthur E. Jacobson、Richard B. Rothman、Christina M. Dersch、Heng Xu、Frank Porreca、Kenner C. Rice

  DOI：10.1021/jm0001222

  日期：2000.8.1

  Potent, selective, and efficacious delta-opioid receptor agonists such as (+)-4-[(alpha R)-alpha-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide [SNC80, (+)-2] have been found to be useful tools for exploring the structural requirements which are necessary for ligands which interact with the delta-receptor. To determine the necessity for the 4-allyl moiety in (+)-2, this substituent was replaced with a variety of 4-alkyl, 4-arylalkyl, and 4-alkenyl substituents. The corresponding enantiomers of these compounds were also synthesized. The binding affinities for the mu-, delta-, and kappa-opioid receptors and efficacies in the functional GTP gamma S binding assay were determined for the (+)-2 related compounds and their enantiomers. The 4-crotyl analogue was found to have similar delta-receptor affinity and efficacy as (+)-2, but the 4-cyclopropylmethyl analogue, in the functional assay, appeared to be a partial agonist with little antagonist activity.