3-(5-amino-3-methyl-4-isoxazolyl)-1,2,5,6-tetrahydro-1-methylpyridine

• 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: 3-(5-amino-3-methyl-4-isoxazolyl)-1,2,5,6-tetrahydro-1-methylpyridine
• 英文别名: 3-methyl-4-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-1,2-oxazol-5-amine
• 化学式: C₁₀H₁₅N₃O
• 分子量: 193.249
• InChiKey: OSTGNBHEUZKVIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-amino-3-methyl-4-isoxazolyl)-1,2,5,6-tetrahydro-1-methylpyridine 在 氢氧化钾 、 ammonium hydroxide 作用下， 以 N-甲基乙酰胺 、 水 、 丙酮 为溶剂， 生成 3-(5-Butylamino-3-methyl-4-isoxazolyl)-1,2,5,6-tetrahydro-1-methylpyridine oxalate
  参考文献：
  名称：

  Substituted azacyclic compounds

  摘要：

  本发明涉及治疗活性杂环化合物，以及其制备方法和包含这些化合物的药物组合物。这些新型化合物在治疗与尼古丁胆碱系统功能失调有关的中枢神经系统疾病方面具有用途。

  公开号：

  US05994373A1
• 作为产物：
  描述：

  3-吡啶乙腈 在 sodium tetrahydroborate 、 盐酸羟胺 作用下， 反应 1.5h， 生成 3-(5-amino-3-methyl-4-isoxazolyl)-1,2,5,6-tetrahydro-1-methylpyridine
  参考文献：
  名称：

  3-(5-Alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridines: a novel class of central nicotinic receptor ligands

  摘要：

  A novel class of central nicotinic acetylcholine receptor ligands, 3-(5-alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridine 4a-f, was synthesized. Several of the compounds showed high affinity for central nicotinic receptors (4c: IC50 = 50 nM), with more than a 100-fold selectivity for nicotinic over muscarinic receptors. The compounds showed up to a 10-fold selectivity for the central nicotinic subtype combination alpha 4 beta 2 (4c: IC50 = 4.6 nM), as compared to the major ganglionic subtype composed of alpha 3 containing subunits (4c: IC50 = 48 nM). The compounds were further evaluated in a dopamine release assay in vitro, and in a drug discrimination assay in vivo. Compound 4a is an effective nicotinic agonist with a potency 50-100 times lower than nicotine. Extending the alkylamino chain beyond one, compound (4b-f), changed the pharmacological profile of the compounds in an antagonistic direction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00101-1

文献信息

• NOVEL SUBSTITUTED AZACYCLIC COMPOUNDS
  申请人：NOVO NORDISK A/S

  公开号：EP0835255A1

  公开（公告）日：1998-04-15
• US5994373A
  申请人：——

  公开号：US5994373A

  公开（公告）日：1999-11-30
• [EN] NOVEL SUBSTITUTED AZACYCLIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES AZACYCLIQUES SUBSTITUES
  申请人：NOVO NORDISK A/S

  公开号：WO1997001555A1

  公开（公告）日：1997-01-16

  (EN) The present invention relates to therapeutically active heterocyclic compounds, to methods for their preparation and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system related to malfunctioning of the nicotinic cholinergic system.(FR) L'invention porte sur des composés hétérocycliques à activité thérapeutique, sur leur procédé de préparation, et sur des compositions pharmaceutiques les contenant. Ces nouveaux composés peuvent servir à traiter des maladies du système nerveux central en relation avec un dysfonctionnement du système cholinergique nicotinique.
• 3-(5-Alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridines: a novel class of central nicotinic receptor ligands
  作者：Preben H. Olesen、Michael D.B. Swedberg、Karin Rimvall

  DOI：10.1016/s0968-0896(98)00101-1

  日期：1998.9

  A novel class of central nicotinic acetylcholine receptor ligands, 3-(5-alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridine 4a-f, was synthesized. Several of the compounds showed high affinity for central nicotinic receptors (4c: IC50 = 50 nM), with more than a 100-fold selectivity for nicotinic over muscarinic receptors. The compounds showed up to a 10-fold selectivity for the central nicotinic subtype combination alpha 4 beta 2 (4c: IC50 = 4.6 nM), as compared to the major ganglionic subtype composed of alpha 3 containing subunits (4c: IC50 = 48 nM). The compounds were further evaluated in a dopamine release assay in vitro, and in a drug discrimination assay in vivo. Compound 4a is an effective nicotinic agonist with a potency 50-100 times lower than nicotine. Extending the alkylamino chain beyond one, compound (4b-f), changed the pharmacological profile of the compounds in an antagonistic direction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Substituted azacyclic compounds
  申请人：Novo Nordisk A/S Novo Alle DK 2880

  公开号：US05994373A1

  公开（公告）日：1999-11-30

  The present invention relates to therapeutically active heterocyclic compounds, to methods for their preparation and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system related to malfunctioning of the nicotinic cholinergic system.

  本发明涉及治疗活性杂环化合物，以及其制备方法和包含这些化合物的药物组合物。这些新型化合物在治疗与尼古丁胆碱系统功能失调有关的中枢神经系统疾病方面具有用途。