(±)-3-(dimethylamino)-N-ethylpyrrolidine-1-carboxamide

• 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: (±)-3-(dimethylamino)-N-ethylpyrrolidine-1-carboxamide
• 英文别名: 3-(dimethylamino)-N-ethylpyrrolidine-1-carboxamide
• 化学式: C₉H₁₉N₃O
• 分子量: 185.269
• InChiKey: FZSZKMMXRBDBQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(二甲氨基)吡咯烷 、 异氰酸乙酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以62%的产率得到(±)-3-(dimethylamino)-N-ethylpyrrolidine-1-carboxamide
  参考文献：
  名称：

  Conformationally restrained carbamoylcholine homologues. Synthesis, pharmacology at neuronal nicotinic acetylcholine receptors and biostructural considerations

  摘要：

  Exploration of small selective ligands for the nicotinic acetylcholine receptors (nAChRs) based on acetylcholine (ACh) has led to the development of potent agonists with clear preference for the 042 nAChR, the most prevalent nAChR subtype in the central nervous system. In this work we present the continuation of these efforts aimed at increasing this subtype selectivity by introduction of conformational restriction in the carbamoylcholine homologue, 3-(dimethylaminobutyl) dimethylcarbamate (DMABC). Our results highlight the importance of the N-carbamoyl substitution in alpha(4)beta(2)-subtype selectivity. Moreover, we have confirmed the non-linear conformation of DMABC bound to nAChRs suggested by recent crystal structures of the compound in complex with the Lymnaea stagnalis ACh binding protein. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.029

文献信息

• [EN] AMINO - PYRIMIDINE COMPOUNDS AS INHIBITORS OF TBKL AND/OR IKK EPSILON<br/>[FR] COMPOSÉS D'AMINO-PYRIMIDINE EN TANT QU'INHIBITEURS DE TBKL ET OU D'IKK EPSILON
  申请人：MYREXIS INC

  公开号：WO2011046970A1

  公开（公告）日：2011-04-21

  The invention relates to certain amino-pyrimidine compounds which inhibit TBK1 and/or IKK epsilon and which may therefore find application in treating inflammation, cancer, septic shock and/or Primary open Angle Glaucoma (POAG).

  这项发明涉及抑制TBK1和/或IKK epsilon的某些氨基嘧啶化合物，因此可能在治疗炎症、癌症、感染性休克和/或原发性开角青光眼（POAG）中找到应用。
• Conformationally restrained carbamoylcholine homologues. Synthesis, pharmacology at neuronal nicotinic acetylcholine receptors and biostructural considerations
  作者：Mario de la Fuente Revenga、Thomas Balle、Anders A. Jensen、Bente Frølund

  DOI：10.1016/j.ejmech.2015.07.029

  日期：2015.9

  Exploration of small selective ligands for the nicotinic acetylcholine receptors (nAChRs) based on acetylcholine (ACh) has led to the development of potent agonists with clear preference for the 042 nAChR, the most prevalent nAChR subtype in the central nervous system. In this work we present the continuation of these efforts aimed at increasing this subtype selectivity by introduction of conformational restriction in the carbamoylcholine homologue, 3-(dimethylaminobutyl) dimethylcarbamate (DMABC). Our results highlight the importance of the N-carbamoyl substitution in alpha(4)beta(2)-subtype selectivity. Moreover, we have confirmed the non-linear conformation of DMABC bound to nAChRs suggested by recent crystal structures of the compound in complex with the Lymnaea stagnalis ACh binding protein. (C) 2015 Elsevier Masson SAS. All rights reserved.