ethyl 1-(tert-butoxycarbonyl)-4-amino-2,5-dihydro-1H-pyrrole-3-carboxylate | 951626-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: ethyl 1-(tert-butoxycarbonyl)-4-amino-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: 1-tert-butyl O3-ethyl 4-amino-2,5-dihydropyrrole-1,3-dicarboxylate；1-Tert-butyl 3-ethyl 4-amino-1H-pyrrole-1,3(2H,5H)-dicarboxylate；1-O-tert-butyl 3-O-ethyl 4-amino-2,5-dihydropyrrole-1,3-dicarboxylate
• CAS: 951626-01-0
• 化学式: C₁₂H₂₀N₂O₄
• 分子量: 256.302
• InChiKey: OLAJVEXJZWCPEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-(tert-butoxycarbonyl)-4-amino-2,5-dihydro-1H-pyrrole-3-carboxylate 在 吡啶 、 盐酸 、 sodium ethanolate 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 65.5h， 生成 (S)-1-[2'-amino-2'-carboxyethyl]-6-methyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2,4(1H,3H)-dione
  参考文献：
  名称：

  (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements and Structural and Biological Investigation

  摘要：

  Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAP. analysis. Interesting binding properties at GluA2, G1uK1, and G1uK3 receptors were discovered. The requirements for G1uK3 interaction were elucidated by determining the X-ray structures of the GluK3-LBD with 2 and Sc and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).

  DOI：

  10.1021/acs.jmedchem.8b00099
• 作为产物：
  描述：

  N-BOC-甘氨酸乙酯 在 ammonium acetate 、 sodium hydride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 17.0h， 生成 ethyl 1-(tert-butoxycarbonyl)-4-amino-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements and Structural and Biological Investigation

  摘要：

  Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAP. analysis. Interesting binding properties at GluA2, G1uK1, and G1uK3 receptors were discovered. The requirements for G1uK3 interaction were elucidated by determining the X-ray structures of the GluK3-LBD with 2 and Sc and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).

  DOI：

  10.1021/acs.jmedchem.8b00099

文献信息

• [EN] IMIDAZOLE MACROCYCLES FOR THE TREATMENT OF AUTOIMMUNE DISEASE<br/>[FR] MACROCYCLES D'IMIDAZOLE POUR LE TRAITEMENT D'UNE MALADIE AUTO-IMMUNE
  申请人：[en]F. HOFFMANN-LA ROCHE AG

  公开号：WO2023148129A1

  公开（公告）日：2023-08-10

  The present invention relates to compounds of formula (Ia), (Ia), wherein R2, M1, M2, M3, Q1and Q2are as described herein, and their pharmaceutically acceptable salt thereof, and compositions including the compounds and methods of using the compounds.
• (<i>S</i>)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements and Structural and Biological Investigation
  作者：Simone Brogi、Margherita Brindisi、Stefania Butini、Giridhar U. Kshirsagar、Samuele Maramai、Giulia Chemi、Sandra Gemma、Giuseppe Campiani、Ettore Novellino、Paolo Fiorenzani、Jessica Pinassi、Anna Maria Aloisi、Mikko Gynther、Raminta Venskutonytė、Liwei Han、Karla Frydenvang、Jette Sandholm Kastrup、Darryl S. Pickering

  DOI：10.1021/acs.jmedchem.8b00099

  日期：2018.3.8

  Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAP. analysis. Interesting binding properties at GluA2, G1uK1, and G1uK3 receptors were discovered. The requirements for G1uK3 interaction were elucidated by determining the X-ray structures of the GluK3-LBD with 2 and Sc and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).