3-chloro-N-(2-methoxyethyl)-N-((1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-yl)thiophene-2-carboxamide | 1144040-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-chloro-N-(2-methoxyethyl)-N-((1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-yl)thiophene-2-carboxamide
• 英文别名: 3-chloro-N-(2-methoxyethyl)-N-[(1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-yl]thiophene-2-carboxamide
• CAS: 1144040-74-3
• 化学式: C₂₈H₃₀ClN₃O₂S
• 分子量: 508.084
• InChiKey: VYQHDBXDUIVOEH-CLJLJLNGSA-N

物化性质

• 沸点：
  683.2±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,2R)-N-(2-methoxyethyl)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-amine 、 3-氯噻吩-2-甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到3-chloro-N-(2-methoxyethyl)-N-((1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  Discovery of μ-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions

  摘要：

  A series of 1-aminotetralin scaffolds was synthesized via metal-catalyzed ring-opening reactions of heterobicyclic alkenes. Small libraries of amides and amines were made using the amino group of each scaffold as a handle. Screening of these libraries against human opioid receptors led to the identification of (S)-(S)-5.2a as a high-affinity selective mu ligand (IC50 mu = 5 nM, kappa = 707 nM, delta = 3,795 nM) displaying mu-agonist/antagonist properties due to its partial agonism (EC50 = 2.6 mu M; E-max = 18%). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.095

文献信息

• Discovery of μ-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions
  作者：Chris Dockendorff、Shujuan Jin、Madeline Olsen、Mark Lautens、Martin Coupal、Lejla Hodzic、Nathan Spear、Kemal Payza、Christopher Walpole、Mirosław J. Tomaszewski

  DOI：10.1016/j.bmcl.2008.12.095

  日期：2009.2

  A series of 1-aminotetralin scaffolds was synthesized via metal-catalyzed ring-opening reactions of heterobicyclic alkenes. Small libraries of amides and amines were made using the amino group of each scaffold as a handle. Screening of these libraries against human opioid receptors led to the identification of (S)-(S)-5.2a as a high-affinity selective mu ligand (IC50 mu = 5 nM, kappa = 707 nM, delta = 3,795 nM) displaying mu-agonist/antagonist properties due to its partial agonism (EC50 = 2.6 mu M; E-max = 18%). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.