7-acryloyl-7-aza-1,4-dioxadispiro[4.0.4.3]tridecan-9-en-8-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-acryloyl-7-aza-1,4-dioxadispiro[4.0.4.3]tridecan-9-en-8-one
• 英文别名: 4-Prop-2-enoyl-7,10-dioxa-4-azadispiro[4.0.46.35]tridec-1-en-3-one；4-prop-2-enoyl-7,10-dioxa-4-azadispiro[4.0.46.35]tridec-1-en-3-one
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: HXCDLPFSLMUXNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-acryloyl-7-aza-1,4-dioxadispiro[4.0.4.3]tridecan-9-en-8-one 、 3-哌啶甲酸乙酯 以 甲醇 为溶剂， 以70%的产率得到ethyl 1-[3-(8-oxo-7-aza-1,4-dioxadispiro[4.0.4.3]tridecan-9-en-7-yl)-3-oxopropyl]piperidine-3-carboxylate
  参考文献：
  名称：

  Straightforward and effective synthesis of γ-aminobutyric acid transporter subtype 2-selective acyl-substituted azaspiro[4.5]decanes

  摘要：

  Supply of major metabolites such as gamma-aminobutyric acid (GABA), beta-alanine and taurine is an essential instrument that shapes signalling, proper cell functioning and survival in the brain and peripheral organs. This background motivates the synthesis of novel classes of compounds regulating their selective transport through various fluid-organ barriers via the low-affinity gamma-aminobutyric acid (GABA) transporter subtype 2 (GAT2). Natural and synthetic spirocyclic compounds or therapeutics with a range of structures and biological activity are increasingly recognised in this regard. Based on pre-validated GABA transport activity, straightforward and efficient synthesis method was developed to provide an azaspiro[4.5]decane scaffold, holding a variety of charge, substituent and 3D constrain of spirocyclic amine. Investigation of the azaspiro[4.5]decane scaffold in cell lines expressing the four GABA transporter subtypes led to the discovery of a subclass of a GAT2-selective compounds with acyl-substituted azaspiro[4.5]decane core. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.100
• 作为产物：
  描述：

  在 aluminum (III) chloride 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 7-acryloyl-7-aza-1,4-dioxadispiro[4.0.4.3]tridecan-9-en-8-one
  参考文献：
  名称：

  Straightforward and effective synthesis of γ-aminobutyric acid transporter subtype 2-selective acyl-substituted azaspiro[4.5]decanes

  摘要：

  Supply of major metabolites such as gamma-aminobutyric acid (GABA), beta-alanine and taurine is an essential instrument that shapes signalling, proper cell functioning and survival in the brain and peripheral organs. This background motivates the synthesis of novel classes of compounds regulating their selective transport through various fluid-organ barriers via the low-affinity gamma-aminobutyric acid (GABA) transporter subtype 2 (GAT2). Natural and synthetic spirocyclic compounds or therapeutics with a range of structures and biological activity are increasingly recognised in this regard. Based on pre-validated GABA transport activity, straightforward and efficient synthesis method was developed to provide an azaspiro[4.5]decane scaffold, holding a variety of charge, substituent and 3D constrain of spirocyclic amine. Investigation of the azaspiro[4.5]decane scaffold in cell lines expressing the four GABA transporter subtypes led to the discovery of a subclass of a GAT2-selective compounds with acyl-substituted azaspiro[4.5]decane core. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.100

文献信息

• Straightforward and effective synthesis of γ-aminobutyric acid transporter subtype 2-selective acyl-substituted azaspiro[4.5]decanes
  作者：Xiaofeng Ma、Hodney Lubin、Enikő Ioja、Orsolya Kékesi、Ágnes Simon、Ágota Apáti、Tamás I. Orbán、László Héja、Julianna Kardos、István E. Markó

  DOI：10.1016/j.bmcl.2015.11.100

  日期：2016.1

  Supply of major metabolites such as gamma-aminobutyric acid (GABA), beta-alanine and taurine is an essential instrument that shapes signalling, proper cell functioning and survival in the brain and peripheral organs. This background motivates the synthesis of novel classes of compounds regulating their selective transport through various fluid-organ barriers via the low-affinity gamma-aminobutyric acid (GABA) transporter subtype 2 (GAT2). Natural and synthetic spirocyclic compounds or therapeutics with a range of structures and biological activity are increasingly recognised in this regard. Based on pre-validated GABA transport activity, straightforward and efficient synthesis method was developed to provide an azaspiro[4.5]decane scaffold, holding a variety of charge, substituent and 3D constrain of spirocyclic amine. Investigation of the azaspiro[4.5]decane scaffold in cell lines expressing the four GABA transporter subtypes led to the discovery of a subclass of a GAT2-selective compounds with acyl-substituted azaspiro[4.5]decane core. (C) 2015 Elsevier Ltd. All rights reserved.