2-(3,4-dichlorophenyl)-N-methyl-N-[(1R)-1-(3-aminophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide | 767268-92-8

• 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: 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R)-1-(3-aminophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide
• 英文别名: N-[(R)-1-(3-Amino-phenyl)-2-pyrrolidin-1-yl-ethyl]-2-(3,4-dichloro-phenyl)-N-methyl-acetamide; hydrochloride；N-[(1R)-1-(3-aminophenyl)-2-pyrrolidin-1-ylethyl]-2-(3,4-dichlorophenyl)-N-methylacetamide
• CAS: 767268-92-8
• 化学式: C₂₁H₂₅Cl₂N₃O
• 分子量: 406.355
• InChiKey: GZGGYQMNFMHDFI-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 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：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Fluorescein isothiocyanate 、 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R)-1-(3-aminophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide 以 四氢呋喃 为溶剂， 以80%的产率得到5-{3-[3-((R)-1-{[2-(3,4-Dichloro-phenyl)-acetyl]-methyl-amino}-2-pyrrolidin-1-yl-ethyl)-phenyl]-thioureido}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid
  参考文献：
  名称：

  Arylacetamide kappa-selective opioid ligands

  摘要：

  A family of arylacetamide opioid ligands was prepared. Competition binding studies indicate that in each case the (S)-(+) series was two orders of magnitude more potent than the corresponding (R)-(-) series and that the amine (S)-(+)-3 and the acetamide (S)-(+)-4 were selective for the kappa opioid binding site. Binding and flow cytometry experiments demonstrated that (S)-(+)-FITC-AA 5 was the enantiomer that bound to the re opioid receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00406-x
• 作为产物：
  描述：

  2-(3,4-Dichloro-phenyl)-N-methyl-N-[(R)-1-(3-nitro-phenyl)-2-pyrrolidin-1-yl-ethyl]-acetamide 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以80%的产率得到2-(3,4-dichlorophenyl)-N-methyl-N-[(1R)-1-(3-aminophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide
  参考文献：
  名称：

  Arylacetamide kappa-selective opioid ligands

  摘要：

  A family of arylacetamide opioid ligands was prepared. Competition binding studies indicate that in each case the (S)-(+) series was two orders of magnitude more potent than the corresponding (R)-(-) series and that the amine (S)-(+)-3 and the acetamide (S)-(+)-4 were selective for the kappa opioid binding site. Binding and flow cytometry experiments demonstrated that (S)-(+)-FITC-AA 5 was the enantiomer that bound to the re opioid receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00406-x

文献信息

• Diamine compounds
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0325406B1

  公开（公告）日：1993-12-29
• US5229414A
  申请人：——

  公开号：US5229414A

  公开（公告）日：1993-07-20
• US5859043A
  申请人：——

  公开号：US5859043A

  公开（公告）日：1999-01-12
• US6468971B1
  申请人：——

  公开号：US6468971B1

  公开（公告）日：2002-10-22
• Arylacetamide kappa-selective opioid ligands
  作者：Anthony D. Pechulis、Sydney Archer、Mark P. Wentland、Ann M. Colasurdo、Jean M. Bidlack

  DOI：10.1016/s0960-894x(97)00406-x

  日期：1997.9

  A family of arylacetamide opioid ligands was prepared. Competition binding studies indicate that in each case the (S)-(+) series was two orders of magnitude more potent than the corresponding (R)-(-) series and that the amine (S)-(+)-3 and the acetamide (S)-(+)-4 were selective for the kappa opioid binding site. Binding and flow cytometry experiments demonstrated that (S)-(+)-FITC-AA 5 was the enantiomer that bound to the re opioid receptor. (C) 1997 Elsevier Science Ltd.