N-Ethyl-N,6-dimethyl-3-pyridinecarboxamide | 185510-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-Ethyl-N,6-dimethyl-3-pyridinecarboxamide
• 英文别名: N-ethyl-N,6-dimethylpyridine-3-carboxamide
• CAS: 185510-47-8
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: QNASLDXBVDLZEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  313.5±30.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Ethyl-N,6-dimethyl-3-pyridinecarboxamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 6-methyl-3-(N-ethyl-N-methylaminomethyl)pyridine
  参考文献：
  名称：

  Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation

  摘要：

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.

  DOI：

  10.1016/s0223-5234(97)89850-9
• 作为产物：
  描述：

  6-甲基烟酸 、 N-乙基甲基胺 在 氯甲酸乙酯 、 三乙胺 作用下， 生成 N-Ethyl-N,6-dimethyl-3-pyridinecarboxamide
  参考文献：
  名称：

  Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation

  摘要：

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.

  DOI：

  10.1016/s0223-5234(97)89850-9

文献信息

• AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION
  申请人：C4 Therapeutics, Inc.

  公开号：US20190076539A1

  公开（公告）日：2019-03-14

  This invention provides amine-linked C 3 -glutarimide Degronimers and Degrons for therapeutic applications as described further herein, and methods of use and compositions thereof as well as methods for their preparation.