4-methyl-anabaseine | 156743-50-9

• 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: 4-methyl-anabaseine
• 英文别名: 3-(4-Methyl-2,3,4,5-tetrahydropyridin-6-yl)pyridine
• CAS: 156743-50-9
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: NVXXBYAJVDWDKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-anabaseine 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Spectroscopic Comparison of the Eight Methyl-2,3’-bipyridyls and Identification of a Hoplonemertine Alkaloid as 3-Methyl-2,3’-bipyridyl

  摘要：

  The pyridyl ring is frequently found in natural products and drugs. While bipyridyls have served as useful scaffolds for development of industrial and pesticidal chemicals, their biological properties are still not well understood. Only 2,3'-bipyridyl, of the six isomeric bipyridyls, has been reported as a natural product in tobacco plants and in a hoplonemertine marine worm, Amphiporus angulatus (Aa), which uses its pyridyl alkaloid-rich venom to paralyze its crustacean prey and chemically defend itself against predators. Here we report for the first time the synthesis and spectroscopic properties of all eight possible methyl 2,3'-bipyridyl isomers and use this data to identify a trace alkaloidal constituent of Aa as 3-methyl-2,3'-bipyridyl. This is only the second reported instance of a methyl-bipyridyl being found as a natural product, the first being the tobacco alkaloid 5-methyl-2,3'-bipyridyl.

  DOI：

  10.3987/com-08-s(d)80
• 作为产物：
  描述：

  tert-butyl 4-methyl-2-oxopiperidine-1-carboxylate 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 4.2h， 以70%的产率得到4-methyl-anabaseine
  参考文献：
  名称：

  WO2006/133303

  摘要：

  公开号：

文献信息

• ALPHA 7 NICOTINIC RECEPTOR SELECTIVE LIGANDS
  申请人：Kem William R.

  公开号：US20120094943A1

  公开（公告）日：2012-04-19

  The invention relates to the design and synthesis of 3-arylidene-anabaseine compounds that exhibit enhanced selectivity toward alpha7 nicotinic receptors. The compounds are expected to be useful in treating a wide variety of conditions, including neurodegenerative conditions such as Alzheimer's Disease, neurodevelopmental diseases such as schizophrenia, and certain peripherally located inflammations mediated by macrophage infiltration.

  本发明涉及设计和合成3-芳基亚胺基烟碱化合物，这些化合物表现出对α7烟碱受体的增强选择性。这些化合物预计可用于治疗各种疾病，包括神经退行性疾病，如阿尔茨海默病，神经发育性疾病，如精神分裂症，以及由巨噬细胞浸润介导的某些周围炎症。
• Alpha 7 Nicotinic Receptor Selective Ligands
  申请人：Kem William R.

  公开号：US20090215705A1

  公开（公告）日：2009-08-27

  The invention relates to the design and synthesis of 3-arylidene-anabaseine compounds that exhibit enhanced selectivity toward alpha7 nicotinic receptors. The compounds are expected to be useful in treating a wide variety of conditions, including neurodegenerative conditions such as Alzheimer's Disease, neurodevelopmental diseases such as schizophrenia, and certain peripherally located inflammations mediated by macrophage infiltration.

  该发明涉及设计和合成3-芳基亚基胆碱碱化物化合物，该化合物对α7尼古丁受体具有增强选择性。这些化合物预计可用于治疗各种疾病，包括神经退行性疾病，如阿尔茨海默病，神经发育性疾病，如精神分裂症，以及由巨噬细胞浸润介导的某些周围部位的炎症。
• US8093269B2
  申请人：——

  公开号：US8093269B2

  公开（公告）日：2012-01-10
• Synthesis and Spectroscopic Comparison of the Eight Methyl-2,3’-bipyridyls and Identification of a Hoplonemertine Alkaloid as 3-Methyl-2,3’-bipyridyl
  作者：William R. Kem、H. Martin Garraffo、Thomas F. Spande、John W. Daly、Ferenc Sóti、James Rocca

  DOI：10.3987/com-08-s(d)80

  日期：——

  The pyridyl ring is frequently found in natural products and drugs. While bipyridyls have served as useful scaffolds for development of industrial and pesticidal chemicals, their biological properties are still not well understood. Only 2,3'-bipyridyl, of the six isomeric bipyridyls, has been reported as a natural product in tobacco plants and in a hoplonemertine marine worm, Amphiporus angulatus (Aa), which uses its pyridyl alkaloid-rich venom to paralyze its crustacean prey and chemically defend itself against predators. Here we report for the first time the synthesis and spectroscopic properties of all eight possible methyl 2,3'-bipyridyl isomers and use this data to identify a trace alkaloidal constituent of Aa as 3-methyl-2,3'-bipyridyl. This is only the second reported instance of a methyl-bipyridyl being found as a natural product, the first being the tobacco alkaloid 5-methyl-2,3'-bipyridyl.
• WO2006/133303
  申请人：——

  公开号：——

  公开（公告）日：——