7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptanoic acid | 873445-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptanoic acid
• CAS: 873445-18-2
• 化学式: C₂₀H₂₆N₂O₂
• 分子量: 326.439
• InChiKey: GTWGNJRNQJSNSN-UHFFFAOYSA-N

物化性质

• 沸点：
  567.8±50.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptanoic acid 、 色胺盐酸盐 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以44%的产率得到7-(1,2,3,4-Tetrahydro-acridin-9-ylamino)-heptanoic acid [2-(1H-indol-3-yl)-ethyl]-amide
  参考文献：
  名称：

  Novel Tacrine−Melatonin Hybrids as Dual-Acting Drugs for Alzheimer Disease, with Improved Acetylcholinesterase Inhibitory and Antioxidant Properties

  摘要：

  Tacrine and melatonin are well-known drugs with activities as an acetylcholinesterase (AChE) inhibitor and free radical scavenger, respectively. In this work, we report new hybrids of both drugs that display higher in vitro properties than the sum of their parts. As selective inhibitors of human AChE, their IC50 values range from sub-nanomolar to picomolar. They exhibit a higher oxygen radical absorbance capacity than does melatonin and are predicted to be able to cross the blood-brain barrier to reach their targets in the central nervous system.

  DOI：

  10.1021/jm050746d
• 作为产物：
  描述：

  9-氯-1,2,3,4-四氢吖啶 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.75h， 生成 7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptanoic acid
  参考文献：
  名称：

  Histone deacetylase inhibitors based on derivatives of tricyclic polyhydroacridine and analogs possessing fused saturated five- and seven-membered rings

  摘要：

  本发明涉及式(I)的化合物，以及它们的制备方法、包含相同化合物的药物组合物，以及用于治疗和/或化学预防癌症、血液恶性肿瘤、增殖性疾病、神经系统疾病和免疫系统疾病的用途。

  公开号：

  EP2801569A1

文献信息

• Histone deacetylase inhibitors based on derivatives of tricyclic polyhydroacridine and analogs possessing fused saturated five- and seven-membered rings
  申请人：Ikerchem, S.L.

  公开号：EP2801569A1

  公开（公告）日：2014-11-12

  The present invention refers to compounds of formula (I): as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or chemoprevention of cancer hematological malignancy, proliferative diseases, neurological disorders and immunological disorders.

  本发明涉及式(I)的化合物，以及它们的制备方法、包含相同化合物的药物组合物，以及用于治疗和/或化学预防癌症、血液恶性肿瘤、增殖性疾病、神经系统疾病和免疫系统疾病的用途。
• Novel Tacrine−Melatonin Hybrids as Dual-Acting Drugs for Alzheimer Disease, with Improved Acetylcholinesterase Inhibitory and Antioxidant Properties
  作者：María Isabel Rodríguez-Franco、María Isabel Fernández-Bachiller、Concepción Pérez、Blanca Hernández-Ledesma、Begoña Bartolomé

  DOI：10.1021/jm050746d

  日期：2006.1.1

  Tacrine and melatonin are well-known drugs with activities as an acetylcholinesterase (AChE) inhibitor and free radical scavenger, respectively. In this work, we report new hybrids of both drugs that display higher in vitro properties than the sum of their parts. As selective inhibitors of human AChE, their IC50 values range from sub-nanomolar to picomolar. They exhibit a higher oxygen radical absorbance capacity than does melatonin and are predicted to be able to cross the blood-brain barrier to reach their targets in the central nervous system.