1,3-di-tert-butyl 2-(2-{[1-(tert-butoxycarbonyl)azepane-4-yl]amino}phenyl)propanedioate | 1422035-97-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3-di-tert-butyl 2-(2-{[1-(tert-butoxycarbonyl)azepane-4-yl]amino}phenyl)propanedioate
• CAS: 1422035-97-9
• 化学式: C₂₈H₄₄N₂O₆
• 分子量: 504.667
• InChiKey: JOQCQAGRFNUKSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-di-tert-butyl 2-(2-{[1-(tert-butoxycarbonyl)azepane-4-yl]amino}phenyl)propanedioate 在 乙基苯磺酸 、 二碳酸二叔丁酯 、 三乙胺 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 以50%的产率得到tert-butyl 4-(2-oxo-2,3-dihydro-1H-indol-1-yl)azepane-1-carboxylate
  参考文献：
  名称：

  Discovery of NovelN-Substituted Oxindoles as Selective M₁and M₄Muscarinic Acetylcholine Receptors Partial Agonists

  摘要：

  Activation of the M-1 and M-4 muscarinic acetylcholine receptors is thought to play an important role in improving the symptoms of schizophrenia. However, discovery of selective agonists for these receptors has been a challenge, considering the high sequence homology and conservation of the orthosteric acetylcholine binding site among muscarinic acetylcholine receptor subtypes. We report in this study the discovery of novel N-substituted oxindoles as potent muscarinic acetylcholine receptor partial agonists selective for M-1 and M-4 over M-2, M-3, and M-5. Among these oxindoles, compound 1 showed high selectivity for the M-1 and M-4 receptors with remarkable penetration into the central nervous system. Compound 1 reversed methamphetamine- and apomorphine-induced psychosis-like behaviors with low potency to extrapyramidical and peripheral side effects.

  DOI：

  10.1021/ml300372f
• 作为产物：
  描述：

  4-氧代氮杂环庚烷-1-羧酸叔丁酯 、 di-t-butyl 2-(2-aminophenyl)malonate 在 titanium(IV)isopropoxide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到1,3-di-tert-butyl 2-(2-{[1-(tert-butoxycarbonyl)azepane-4-yl]amino}phenyl)propanedioate
  参考文献：
  名称：

  Discovery of NovelN-Substituted Oxindoles as Selective M₁and M₄Muscarinic Acetylcholine Receptors Partial Agonists

  摘要：

  Activation of the M-1 and M-4 muscarinic acetylcholine receptors is thought to play an important role in improving the symptoms of schizophrenia. However, discovery of selective agonists for these receptors has been a challenge, considering the high sequence homology and conservation of the orthosteric acetylcholine binding site among muscarinic acetylcholine receptor subtypes. We report in this study the discovery of novel N-substituted oxindoles as potent muscarinic acetylcholine receptor partial agonists selective for M-1 and M-4 over M-2, M-3, and M-5. Among these oxindoles, compound 1 showed high selectivity for the M-1 and M-4 receptors with remarkable penetration into the central nervous system. Compound 1 reversed methamphetamine- and apomorphine-induced psychosis-like behaviors with low potency to extrapyramidical and peripheral side effects.

  DOI：

  10.1021/ml300372f