N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide | 527683-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide
• 英文别名: N-[(3R,5R)-1-azabicyclo[3.2.1]octan-3-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide
• CAS: 527683-31-4；1043687-65-5
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: HOIGWVJGKSSPAR-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 N-[(3R,5R)-1-Azabicyclo[3.2.1]oct-3-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide hydrochloride
  参考文献：
  名称：

  Discovery of N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide as an agonist of the α7 nicotinic acetylcholine receptor: In vitro and in vivo activity

  摘要：

  A novel alpha 7 nAChR agonist, N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide ( 3a, PHA-709829), has been identified for the potential treatment of cognitive deficits in schizophrenia. The compound shows potent and selective a7 in vitro activity, excellent brain penetration, good rat oral bioavailability and robust in vivo efficacy in a rat auditory sensory gating model. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.070
• 作为产物：
  描述：

  2,3-二氢-1,4-苯并二噁烷-6-羧酸 、 (3R,5R)-1-azabicyclo[3.2.1]octan-3-amine dihydrochloride 在 O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide
  参考文献：
  名称：

  Discovery of N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide as an agonist of the α7 nicotinic acetylcholine receptor: In vitro and in vivo activity

  摘要：

  A novel alpha 7 nAChR agonist, N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide ( 3a, PHA-709829), has been identified for the potential treatment of cognitive deficits in schizophrenia. The compound shows potent and selective a7 in vitro activity, excellent brain penetration, good rat oral bioavailability and robust in vivo efficacy in a rat auditory sensory gating model. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.070

文献信息

• Azabicyclic-phenyl-fused-heterocyclic compounds for treatment of disease
  申请人：——

  公开号：US20030130305A1

  公开（公告）日：2003-07-10

  The invention provides compounds of Formula I: 1 wherein Azabicyclo is any of: 2 These compounds may be in the form of pharmaceutical salts or compositions, and racemic mixtures or pure enantiomers thereof. The compounds of Formula I are useful in pharmaceuticals in which &agr;7 is known to be involved.

  这项发明提供了公式I:1中的化合物，其中Azabicyclo是其中的任何一个：2。这些化合物可以是药物盐或组合物的形式，以及它们的外消旋混合物或纯对映体。公式I中的化合物在已知α7参与的药物中是有用的。
• AZABICYCLIC-PHENYL-FUSED-HETEROCYCLIC COMPOUNDS AND THEIR USE AS ALPHA7 NACHR LIGANDS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1442037A1

  公开（公告）日：2004-08-04
• US6951868B2
  申请人：——

  公开号：US6951868B2

  公开（公告）日：2005-10-04
• [EN] AZABICYCLIC-PHENYL-FUSED-HETEROCYCLIC COMPOUNDS AND THEIR USE AS ALPHA7 NACHR LIGANDS<br/>[FR] COMPOSES HETEROCYCLIQUES FUSIONNES AVEC UN GROUPE PHENYL-AZABICYCLIQUE ET LEUR UTILISATION EN TANT QUE LIGANDS DE RECEPTEUR NACHR ALPHA 7
  申请人：UPJOHN CO

  公开号：WO2003042210A1

  公开（公告）日：2003-05-22

  The invention provides compounds of Formula (I): wherein Azabicyclo is any of Formulae (l, II, III, IV, V, VI). These compounds may be in the form of pharmaceutical salts or compositions, and racemic mixtures or pure enantiomers thereof. The compounds of Formula I are useful in pharmaceuticals in which α7 is known to be involved.
• Discovery of N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide as an agonist of the α7 nicotinic acetylcholine receptor: In vitro and in vivo activity
  作者：Brad A. Acker、E. Jon Jacobsen、Bruce N. Rogers、Donn G. Wishka、Steven C. Reitz、David W. Piotrowski、Jason K. Myers、Mark L. Wolfe、Vincent E. Groppi、Bruce A. Thornburgh、Paula M. Tinholt、Rodney R. Walters、Barbara A. Olson、Laura Fitzgerald、Brian A. Staton、Thomas J. Raub、Michael Krause、Kai S. Li、William E. Hoffmann、Mihaly Hajos、Raymond S. Hurst、Daniel P. Walker

  DOI：10.1016/j.bmcl.2008.04.070

  日期：2008.6

  A novel alpha 7 nAChR agonist, N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide ( 3a, PHA-709829), has been identified for the potential treatment of cognitive deficits in schizophrenia. The compound shows potent and selective a7 in vitro activity, excellent brain penetration, good rat oral bioavailability and robust in vivo efficacy in a rat auditory sensory gating model. (C) 2008 Elsevier Ltd. All rights reserved.