1-((1R,5S)-3,7-diazabicyclo[3.3.1]nonan-3-yl)-3-(3-methoxyphenyl)prop-2-yn-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-((1R,5S)-3,7-diazabicyclo[3.3.1]nonan-3-yl)-3-(3-methoxyphenyl)prop-2-yn-1-one
• 英文别名: 1-[(1S,5R)-3,7-diazabicyclo[3.3.1]nonan-3-yl]-3-(3-methoxyphenyl)prop-2-yn-1-one
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: MRFNUTGCMHHOLI-GASCZTMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((1R,5S)-3,7-diazabicyclo[3.3.1]nonan-3-yl)-3-(3-methoxyphenyl)prop-2-yn-1-one 、 富马酸 以 乙醚 、 异丙醇 为溶剂， 以67%的产率得到1-((1R,5S)-3,7-diazabicyclo[3.3.1]nonan-3-yl)-3-(3-methoxyphenyl)prop-2-yn-1-one fumaric acid salt
  参考文献：
  名称：

  The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor ligands. Part 2: Carboxamide derivatives with different spacer motifs

  摘要：

  3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the alpha 4 beta 2* nAChR. Compounds 15, 25, and 47 with K-i values of about 1 nM displayed the highest affinities for alpha 4 beta 2* nAChR. All evaluated compounds are partial agonists or antagonists at alpha 4 beta 2*, with reduced or no effects on alpha 3 beta 4* with the exception of compound 15 (agonist), and reduced or no effect at alpha 7 and muscle subtypes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.060
• 作为产物：
  描述：

  以 1,4-二氧六环 为溶剂， 反应 2.0h， 以99%的产率得到1-((1R,5S)-3,7-diazabicyclo[3.3.1]nonan-3-yl)-3-(3-methoxyphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor ligands. Part 2: Carboxamide derivatives with different spacer motifs

  摘要：

  3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the alpha 4 beta 2* nAChR. Compounds 15, 25, and 47 with K-i values of about 1 nM displayed the highest affinities for alpha 4 beta 2* nAChR. All evaluated compounds are partial agonists or antagonists at alpha 4 beta 2*, with reduced or no effects on alpha 3 beta 4* with the exception of compound 15 (agonist), and reduced or no effect at alpha 7 and muscle subtypes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.060

文献信息

• The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor ligands. Part 2: Carboxamide derivatives with different spacer motifs
  作者：Christoph Eibl、Lenka Munoz、Isabelle Tomassoli、Clare Stokes、Roger L. Papke、Daniela Gündisch

  DOI：10.1016/j.bmc.2013.09.060

  日期：2013.12

  3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the alpha 4 beta 2* nAChR. Compounds 15, 25, and 47 with K-i values of about 1 nM displayed the highest affinities for alpha 4 beta 2* nAChR. All evaluated compounds are partial agonists or antagonists at alpha 4 beta 2*, with reduced or no effects on alpha 3 beta 4* with the exception of compound 15 (agonist), and reduced or no effect at alpha 7 and muscle subtypes. (C) 2013 Elsevier Ltd. All rights reserved.