5,6,7,8-tetrahydro-5-hydroxy-2-(phenylmethoxy)-5-(phenylmethyl)quinoline | 143246-84-8

• 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: 5,6,7,8-tetrahydro-5-hydroxy-2-(phenylmethoxy)-5-(phenylmethyl)quinoline
• 英文别名: 5-benzyl-2-phenylmethoxy-7,8-dihydro-6H-quinolin-5-ol
• CAS: 143246-84-8
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: DEFOWRXABFYQRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-5-hydroxy-2-(phenylmethoxy)-5-(phenylmethyl)quinoline 在 硼烷四氢呋喃络合物 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 生成 5,6,7,8-tetrahydro-2-(phenylmethoxy)-5-(phenylmethyl)-5-quinolinamine
  参考文献：
  名称：

  Synthesis and Evaluation of 5-Amino-5,6,7,8-tetrahydroquinolinones as Potential Agents for the Treatment of Alzheimer's Disease

  摘要：

  A series of 5-amino-5,6,7,8-tetrahydroquinolinones was designed and synthesized as acetylcholinesterase inhibitors. The compounds are related to hyperzine A, a naturally occurring cholinesterase inhibitor. They inhibit acetylcholinesterase in vitro, and many are active in vivo in reversing a scopolamine-induced impairment of 24 h memory in a passive avoidance paradigm. Although these compounds were designed as partial structures of huperzine A, it is unlikely that they bind to the enzyme in a similar fashion, since they lack the unsaturated three-carbon bridge of huperzine A and both the quinolinone nitrogen and the amino group must be substituted in order to obtain good enzyme affinity.

  DOI：

  10.1021/jm00018a025
• 作为产物：
  描述：

  7,8-二氢-1H,6H-喹啉-2,5-二酮 在 silver carbonate 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 68.0h， 生成 5,6,7,8-tetrahydro-5-hydroxy-2-(phenylmethoxy)-5-(phenylmethyl)quinoline
  参考文献：
  名称：

  Synthesis and Evaluation of 5-Amino-5,6,7,8-tetrahydroquinolinones as Potential Agents for the Treatment of Alzheimer's Disease

  摘要：

  A series of 5-amino-5,6,7,8-tetrahydroquinolinones was designed and synthesized as acetylcholinesterase inhibitors. The compounds are related to hyperzine A, a naturally occurring cholinesterase inhibitor. They inhibit acetylcholinesterase in vitro, and many are active in vivo in reversing a scopolamine-induced impairment of 24 h memory in a passive avoidance paradigm. Although these compounds were designed as partial structures of huperzine A, it is unlikely that they bind to the enzyme in a similar fashion, since they lack the unsaturated three-carbon bridge of huperzine A and both the quinolinone nitrogen and the amino group must be substituted in order to obtain good enzyme affinity.

  DOI：

  10.1021/jm00018a025

文献信息

• 5-amino-5,6,7,8-tetrahydroquinolines and related compounds and
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05110815A1

  公开（公告）日：1992-05-05

  Novel 5-amino-5,6,7,8-tetrahydroquinolines and related compounds, intermediates and processes for the preparation thereof, and methods for relieving memory dysfunction utilizing compounds or compositions thereof are disclosed.

  揭示了新型5-氨基-5,6,7,8-四氢喹啉及其相关化合物、中间体和制备方法，以及利用这些化合物或组合物缓解记忆功能障碍的方法。
• 5-amino-5,6,7,8-tetrahydroquinolines and related compounds
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05216164A1

  公开（公告）日：1993-06-01

  Novel 5-amino-5,6,7,8-tetrahydroquinolines and related compounds, intermediates and processes for the preparation thereof, and methods for relieving memory dysfunction utilizing compounds or compositions thereof are disclosed.

  本发明披露了新型的5-氨基-5,6,7,8-四氢喹啉及其相关化合物、中间体和制备方法，以及利用这些化合物或组合物缓解记忆功能障碍的方法。
• Process of preparing 5-amino-5,6,7,8-tetrahydroquinolines and related
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05310914A1

  公开（公告）日：1994-05-10

  Novel 5-amino-5,6,7,8-tetrahydroquinolines and related compounds, intermediates and processes for the preparation thereof, and methods for relieving memory dysfunction utilizing compounds or compositions thereof are disclosed.

  本发明公开了一种新型5-氨基-5,6,7,8-四氢喹啉及其相关化合物、中间体和制备方法，以及利用该化合物或其组合物缓解记忆功能障碍的方法。
• 5-amino-5,6,7,8-tetrahydroquinolines and related compounds, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0489379A1

  公开（公告）日：1992-06-10

  The present invention relates to tetrahydroquinolines and related compounds. More particularly, the present invention relates to 5-amino-5,6,7,8-tetrahydroquinolines of the formula wherein X-Y is a group of the formula wherein R is hydrogen, alkyl, alkenyl, alkynyl, or arylalkyl, or a group of the formula wherein R¹ is hydrogen, alkyl or arylalkyl; R² and R³ are independently hydrogen, alkyl, arylalkyl, diarylalkyl, cycloalkenylalkyl, alkoxy, arylalkoxy, or alkanoyl; R² and R³ taken together with the nitrogen atom to which they are attached form a group of the formula wherein p is 0 or 1, a group of the formula wherein Z is O, S, or a group of the formula NR⁶ wherein R⁶ is hydrogen, alkyl, or arylalkyl; R⁴ is hydrogen, alkyl or arylalkyl; R⁵ is hydrogen, alkyl or arylalkyl; and m is 0, 1, or 2, and n is 1 or 2; or geometrical and optical isomers thereof, or a pharmaceutically acceptable salt thereof, which are useful for relieving memory dysfunction, The invention relates further to a process for the preparation of these compounds and their use as medicaments.

  本发明涉及四氢喹啉及相关化合物。更具体地说，本发明涉及式 5-氨基-5,6,7,8-四氢喹啉 其中 X-Y 是式中的基团 其中 R 是氢、烷基、烯基、炔基或芳烷基，或者是式中的基团 其中 R¹ 是氢、烷基或芳基烷基；R² 和 R³ 独立地是氢、烷基、芳基烷基、二芳基烷基、环烯基烷基、烷氧基、芳基烷氧基或烷酰基；R² 和 R³ 与它们所连接的氮原子一起形成式中的基团 式中 p 为 0 或 1 的基团 其中 Z 是 O、S 或式 NR⁶的基团，其中 R⁶ 是氢、烷基或芳基烷基；R⁴ 是氢、烷基或芳基烷基；R⁵ 是氢、烷基或芳基烷基；以及 m 是 0、1 或 2，n 是 1 或 2；或其几何和光学异构体，或其药学上可接受的盐，可用于缓解记忆功能障碍、 本发明还涉及这些化合物的制备工艺及其作为药物的用途。
• US5110815A
  申请人：——

  公开号：US5110815A

  公开（公告）日：1992-05-05