3,5-Dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-tert-butyl ester 2-propyl ester | 528894-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,5-Dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-tert-butyl ester 2-propyl ester
• 英文别名: 3,5-Dimethyl-pyrrole-2,4-dicarboxylic acid 4-t-butyl ester 2-propyl ester
• CAS: 528894-69-1
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: JSMVOAHRTDSKNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  68.39
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,5-Dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-tert-butyl ester 2-propyl ester 在 三氟乙酸 作用下， 反应 0.5h， 以110 mg的产率得到3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-propyl ester
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of 2,4-Dicarboxy-pyrroles as selective non-Competitive mGluR1 antagonists

  摘要：

  Metabotropic glutamate receptors (mGluRs) are an unusual family of G-protein coupled receptor (GPCR), and are characterised by a large extracellular N-terminal domain that contains the glutamate binding site. We have identified a new class of non-competitive metabotropic glutamate receptor 1 (mGluR1) antagonists, 2,4-dicarboxy-pyrroles which are endowed with nano-molar potency. They interact within the 7 transmembrane (7TM) domain of the receptor and show antinociceptive properties when tested in a number of different animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00424-8
• 作为产物：
  描述：

  3,5-二甲基吡咯-2,4-二羧酸2-苄酯4-t-丁酯 在 palladium on activated charcoal 氢气 、 三氟乙酸酐 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 7.0h， 生成 3,5-Dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-tert-butyl ester 2-propyl ester 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of 2,4-Dicarboxy-pyrroles as selective non-Competitive mGluR1 antagonists

  摘要：

  Metabotropic glutamate receptors (mGluRs) are an unusual family of G-protein coupled receptor (GPCR), and are characterised by a large extracellular N-terminal domain that contains the glutamate binding site. We have identified a new class of non-competitive metabotropic glutamate receptor 1 (mGluR1) antagonists, 2,4-dicarboxy-pyrroles which are endowed with nano-molar potency. They interact within the 7 transmembrane (7TM) domain of the receptor and show antinociceptive properties when tested in a number of different animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00424-8

文献信息

• 2,4-Dicarboxy-pyrroles as selective non-Competitive mGluR1 antagonists: further characterization of 3,5-Dimethyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-Trimethyl-propyl) ester and structure–Activity relationships
  作者：Fabrizio Micheli、Romano Di Fabio、Fabio Bordi、Palmina Cavallini、Paolo Cavanni、Daniele Donati、Stefania Faedo、Micaela Maffeis、Fabio Maria Sabbatini、Giorgio Tarzia、Maria Elvira Tranquillini

  DOI：10.1016/s0960-894x(03)00396-2

  日期：2003.7

  Following the disclosure of 3,5-dimethyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl-propyl) ester [3,5-dimethyl PPP] as a potent and selective mGluR1 non-competitive antagonist, we report here further in vivo characterization of this important toot and disclose the investigation of the C-5 position, which led to very potent compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.