N-methyl-N-<(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl>phenylacetamide | 157947-87-0

• 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: N-methyl-N-<(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl>phenylacetamide
• 英文别名: (S)-N-Methyl-2-phenyl-N-(1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide；N-Methyl-N-(1-phenyl-2-(1-pyrrolidinyl)ethyl)phenylacetamide；N-methyl-2-phenyl-N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide
• CAS: 157947-87-0
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: OVZWUDZIAAHNFG-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙酸 、 (S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以95%的产率得到N-methyl-N-<(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl>phenylacetamide
  参考文献：
  名称：

  Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity

  摘要：

  Some K opioid receptor agonists of the arylacetamide class, for example, ICI 199441 (1), were found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50 = 26 nM). Certain analogs bearing a substituted sulfonylamino group, for example, 13, were discovered to have significantly reduced CYP2D6 inhibitory activity (13: CYP2D6 IC50 > 10 mu M) while displaying high affinity toward the cloned human K opioid receptor, good kappa/delta and kappa/mu selectivity, and potent in vitro and in vivo agonist activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.020

文献信息

• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• Analgesic compounds and methods of use
  申请人：The Regents of the University of California

  公开号：US10167295B2

  公开（公告）日：2019-01-01

  Provided herein, inter alia, are methods and compositions for achieving an analgesic effect in subjects in need thereof.

  除其他外，本文还提供了用于在有需要的受试者身上实现镇痛效果的方法和组合物。
• Isothiocyanate-Substituted .kappa.-Selective Opioid Receptor Ligands Derived from N-Methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl]phenylacetamide
  作者：S. Ananda Weerawarna、Ronda D. Davis、Wendel L. Nelson

  DOI：10.1021/jm00044a006

  日期：1994.9

  The synthesis of isothiocyanate-substituted K-selective opioid ligands derived from N-methyl-N-[(1S)-1-phenyl-2- (1-pyrrolidinyl)ethyl]ethyl]phenylacetamide (8) and their effects in radioligand displacement assays are reported. Ligands 3-5 with the S-absolute configuration were prepared with the isothiocyanate functionality at the 2-, 3-, and 4-positions in the phenylacetamide aromatic ring. The 2-isothiocyanato-4,5-dichlorophenylacetamide 6 was prepared to evaluate the effect of 4,5-dichloro substitution in the same aromatic ring as the 2-isothiocyanate function. N-Methyl-N-[(1S)-1-(4-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl]-3,4-dichlorophenylacetamide (7), with the 4-isothiocyanate function in the 1-phenyl ring, was prepared for comparison with the other compounds in the series. Of the prepared ligands, 7 and 8 (IC(50)s similar or equal to 1.4-1.8 nM) were approximately equal in affinity with 2 (ICI-199,441), followed by 3 and 6. All of these compounds were more kappa-selective than 2, as well. The binding characteristics of 8 show that the previously reported 4,5-dichloro substitution is not required for high affinity and kappa-selectivity. All of the synthesized isothiocyanate-substituted ligands irreversibly inhibited radioligand binding to guinea pig brain membrane preparations, including compound 2 (ICI-199,441) which had no isothiocyanate functionality.
• METHODS AND COMPOSITIONS FOR TREATING VASOMOTOR SYMPTOMS
  申请人：UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION

  公开号：US20150272927A1

  公开（公告）日：2015-10-01

  The present disclosure is generally directed to compositions and methods for treating or limiting development of vasomotor symptoms in a subject.
• ANALGESIC COMPOUNDS AND METHODS OF USE
  申请人：The Regents of the University of California

  公开号：US20160068541A1

  公开（公告）日：2016-03-10

  Provided herein, inter alia, are methods and compositions for achieving an analgesic effect in subjects in need thereof.