5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone | 57311-36-1

• 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-1-methyl-5-oxo-2(1H)-quinolinone
• 英文别名: 5,6,7,8-Tetrahydro-1-methyl-5-oxo-2-quinolinone；1-methyl-7,8-dihydro-2,5(1H,6H)-quinolinedione；1-methyl-7,8-dihydro-1H,6H-quinoline-2,5-dione；1-Methyl-2,5-dioxo-1,2,5,6,7,8-hexahydrochinolin；1-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione；1-methyl-7,8-dihydro-6H-quinoline-2,5-dione
• CAS: 57311-36-1
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD03423994
• 分子量: 177.203
• InChiKey: GKMANJNJOGJCNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 85.0h， 生成 5-[[2-(4-trifluoromethylphenyl)ethyl]amino]-5,6,7,8-tetrahydro-1-methyl-2(1H)-quinolinone
  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：

  ethyl 1-methyl-7,8-dihydro-2,5(1H,6H)-quinolinedione-3-carboxylate 、 二甲基亚砜 在 lithium chloride 作用下， 以 水 为溶剂， 生成 5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone
  参考文献：
  名称：

  Pharmaceutical compositions containing quinolin-2,5-diones, new

  摘要：

  这项发明涉及含有式##STR1##的喹啉-2,5-二酮的药物组合物，其中下文定义了A、B、R^1至R^3和X，其中一些是新颖的，这些化合物具有有价值的药理特性，特别是镇痛、退热和/或抗炎作用，以及用于制备它们的新中间体和工艺。

  公开号：

  US05068334A1

文献信息

• Chemotherapeutische Nitroheterocyclen, 17. Mitt.: Kondensationsprodukte von nitrierten heterocyclischen Aldehyden mit Oxo-cyclopentathiophenen und Oxo-tetrahydrochinolinen
  作者：R. Albrecht、E. Schröder

  DOI：10.1002/ardp.19753080803

  日期：——

  Es werden die Kondensationsprodukte 7–22 aus 5‐Nitro‐furfural, 5‐Nitro‐thiophen‐2‐aldehyd, 5‐Nitro‐pyrrol‐2‐aldehyd oder 1‐Methyl‐5‐nitro‐imidazol‐2‐aldehyd und einem Oxo‐cyclopentathiophen oder Oxo‐tetrahydrochinolin hergestellt. Die Verbindungen sind in vitro wirksam gegen Trichomonas vaginalis.

  缩合产物7-22由5-硝基-糠醛、5-硝基-噻吩-2-醛、5-硝基-吡咯-2-醛或1-甲基-5-硝基-咪唑-2-醛和氧代环戊噻吩或氧代四氢喹啉。这些化合物在体外对阴道毛滴虫有活性。
• Dimeric compounds
  申请人：——

  公开号：US20020156096A1

  公开（公告）日：2002-10-24

  The invention relates to dimeric compounds comprising two 5-amino-5,6,7,8-tetrahydroquinoline fragments joined together by a divalent linking group, processes for their preparation, intermediates for their preparation, pharmaceutical compositions containing such dimeric compounds and the use of such compounds as cholinesterase inhibitors and in the treatment of neurodegenerative diseases, such as Alzheimer's Disease and myasthenia gravis.

  这项发明涉及由双价连接基团连接在一起的两个5-氨基-5,6,7,8-四氢喹啉片段构成的二聚化合物，以及其制备方法、制备中间体、含有这种二聚化合物的药物组合物，以及将这种化合物用作胆碱酯酶抑制剂和治疗神经退行性疾病，如阿尔茨海默病和重症肌无力的用途。
• 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。