(3aR,6aS)-5-(pyridin-2-yl)hexahydropyrrole[3,4-c]pyrrole-2(1H)-carboxylate tert-butyl ester | 1173179-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aR,6aS)-5-(pyridin-2-yl)hexahydropyrrole[3,4-c]pyrrole-2(1H)-carboxylate tert-butyl ester
• 英文别名: t-butyl cis-5-(pyridin-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole-2-carboxylate；tert-butyl (3aR,6aS)-2-pyridin-2-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate
• CAS: 1173179-84-4
• 化学式: C₁₆H₂₃N₃O₂
• 分子量: 289.378
• InChiKey: NXSHFQFSZKOPQC-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,6aS)-5-(pyridin-2-yl)hexahydropyrrole[3,4-c]pyrrole-2(1H)-carboxylate tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 为溶剂， 生成 [(3aS,6aR)-2-pyridin-2-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-(3-azaspiro[5.5]undecan-3-yl)methanone
  参考文献：
  名称：

  Octahydropyrrolo[3,4-c]pyrrole negative allosteric modulators of mGlu1

  摘要：

  Development of SAR in an octahydropyrrolo[3,4-c]pyrrole series of negative allosteric modulators of mGlu(1) using a functional cell-based assay is described in this Letter. The octahydropyrrolo[3,4-c]pyrrole scaffold was chosen as an isosteric replacement for the piperazine ring found in the initial hit compound. Characterization of selected compounds in protein binding assays was used to identify the most promising analogs, which were then profiled in P450 inhibition assays in order to further assess the potential for drug-likeness within this series of compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.029
• 作为产物：
  描述：

  2-氯吡啶 、 tert-butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate 在 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以47%的产率得到(3aR,6aS)-5-(pyridin-2-yl)hexahydropyrrole[3,4-c]pyrrole-2(1H)-carboxylate tert-butyl ester
  参考文献：
  名称：

  Octahydropyrrolo[3,4-c]pyrrole: A Diamine Scaffold for Construction of Either α4β2 or α7-Selective Nicotinic Acetylcholine Receptor (nAChR) Ligands. Substitutions that Switch Subtype Selectivity

  摘要：

  A series of 5-(pyridine-3-yl)octahydropyrrolo[3,4-c]pyrroles have been prepared that exhibit high affinity to alpha 4 beta 2 and/or alpha 7 nicotinic acetylcholine receptors (nAChRs). Simple substitution patterns have been identified that allow construction of ligands that are highly selective for either nAChR subtype. The effects of substitution on subtype selectivity provide some insight into the differences in the ligand binding domains of the alpha 4 beta 2 and alpha 7 receptors, especially in regions removed from the cation binding pocket.

  DOI：

  10.1021/jm900249k

文献信息

• Octahydropyrrolo[3,4-<i>c</i>]pyrrole: A Diamine Scaffold for Construction of Either α4β2 or α7-Selective Nicotinic Acetylcholine Receptor (nAChR) Ligands. Substitutions that Switch Subtype Selectivity
  作者：William H. Bunnelle、Karin R. Tietje、Jennifer M. Frost、Dan Peters、Jianguo Ji、Tao Li、Marc J. C. Scanio、Lei Shi、David J. Anderson、Tino Dyhring、Jens H. Grønlien、Hilde Ween、Kirsten Thorin-Hagene、Michael D. Meyer

  DOI：10.1021/jm900249k

  日期：2009.7.23

  A series of 5-(pyridine-3-yl)octahydropyrrolo[3,4-c]pyrroles have been prepared that exhibit high affinity to alpha 4 beta 2 and/or alpha 7 nicotinic acetylcholine receptors (nAChRs). Simple substitution patterns have been identified that allow construction of ligands that are highly selective for either nAChR subtype. The effects of substitution on subtype selectivity provide some insight into the differences in the ligand binding domains of the alpha 4 beta 2 and alpha 7 receptors, especially in regions removed from the cation binding pocket.
• Octahydropyrrolo[3,4-c]pyrrole negative allosteric modulators of mGlu1
  作者：Jason T. Manka、Alice L. Rodriguez、Ryan D. Morrison、Daryl F. Venable、Hyekyung P. Cho、Anna L. Blobaum、J. Scott Daniels、Colleen M. Niswender、P. Jeffrey Conn、Craig W. Lindsley、Kyle A. Emmitte

  DOI：10.1016/j.bmcl.2013.07.029

  日期：2013.9

  Development of SAR in an octahydropyrrolo[3,4-c]pyrrole series of negative allosteric modulators of mGlu(1) using a functional cell-based assay is described in this Letter. The octahydropyrrolo[3,4-c]pyrrole scaffold was chosen as an isosteric replacement for the piperazine ring found in the initial hit compound. Characterization of selected compounds in protein binding assays was used to identify the most promising analogs, which were then profiled in P450 inhibition assays in order to further assess the potential for drug-likeness within this series of compounds. (C) 2013 Elsevier Ltd. All rights reserved.