2-methyl-2H-thiopyran-3,5(4H,6H)-dione | 16855-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2H-thiopyran-3,5(4H,6H)-dione
• 英文别名: 2-Methyl-1-thiocyclohexan-3,5-dion；2-methyl-thiopyran-3,5-dione；2-methylthiane-3,5-dione
• CAS: 16855-83-7
• 化学式: C₆H₈O₂S
• 分子量: 144.194
• InChiKey: UGTNDTQDNGDZAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2H-thiopyran-3,5(4H,6H)-dione 在 lithium aluminium tetrahydride 、 potassium carbonate 、 对甲苯磺酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 10-Amino-3-methyl-3,4-dihydro-1H-2-thia-9-aza-anthracen-4-ol
  参考文献：
  名称：

  Velnacrine thiaanalogues as potential agents for treating alzheimer's disease

  摘要：

  The only therapeutic drugs for combating dementia disease are acetylcholine esterase inhibitors (AChEI). However, the use of tacrine, the first AChEI to be launched as an Alzheimer's disease (AD) drug, has been limited by serious side effects. Therefore, efforts to search for more potent and selective inhibitors of AChE still remain highly significant in the therapeutic treatment of AD. In this work we modified the cyclohexyl ring of velnacrine, a less toxic analogue of tacrine, by synthesizing a series of thiopyranoquinolines in which the C-3 methylene unit was replaced by a sulphur atom. The anti-AChE data show that the activity was maintained with the bioisosteric substitution carried out. The introduction of a chlorine atom at different positions of the aromatic ring resulted in an array of different activities. In an attempt to understand the different behaviours displayed by the chlorine-substituted derivatives, a molecular docking study was performed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00171-7

文献信息

• 4-Acyl-2H-thiopyran-3,5(4H,6H)-diones: Synthesis, Oxidation, and Reaction with Amines
  作者：T. A. Zheldakova、M. V. Budnikova、I. L. Rubinova、D. B. Rubinov

  DOI：10.1023/b:rujo.0000019742.81245.f7

  日期：2003.12

  Acylation of 2H-thiopyran-3,5(4H,6H)-dione and 2-methyl-2H-thiopyran-3,5(4H,6H)-dione with acetyl chloride or propionyl chloride afforded the corresponding 4-acyl-2H-thiopyran-3,5(4H,6H)-diones. Oxidation of 4-acetyl-2H-thiopyran-3,5(4H,6H)-dione with m-chloroperoxybenzoic acid gave 4-acetyl-2H-thiopyran-3,5(4H,6H)-dione I-oxide. 4-Acyl-2H-thiopyran-3,5(4H,6H)-diones and 4-acetyl-2H-thiopyran3,5(4H,6H)-dione I-oxide reacted with pyrrolidine, allylamine, and p-anisidine, resulting in formation of the corresponding 4-aminomethylene derivatives.
• GILKERSON, TERENCE;SHAW, ROBERT WILLIAM;JENNENS, DAVID CLIFFORD
  作者：GILKERSON, TERENCE、SHAW, ROBERT WILLIAM、JENNENS, DAVID CLIFFORD

  DOI：——

  日期：——
• Velnacrine thiaanalogues as potential agents for treating alzheimer's disease
  作者：Oriana Tabarrini、Violetta Cecchetti、Andrea Temperini、Enrica Filipponi、Maria Giuseppina Lamperti、Arnaldo Fravolini

  DOI：10.1016/s0968-0896(01)00171-7

  日期：2001.11

  The only therapeutic drugs for combating dementia disease are acetylcholine esterase inhibitors (AChEI). However, the use of tacrine, the first AChEI to be launched as an Alzheimer's disease (AD) drug, has been limited by serious side effects. Therefore, efforts to search for more potent and selective inhibitors of AChE still remain highly significant in the therapeutic treatment of AD. In this work we modified the cyclohexyl ring of velnacrine, a less toxic analogue of tacrine, by synthesizing a series of thiopyranoquinolines in which the C-3 methylene unit was replaced by a sulphur atom. The anti-AChE data show that the activity was maintained with the bioisosteric substitution carried out. The introduction of a chlorine atom at different positions of the aromatic ring resulted in an array of different activities. In an attempt to understand the different behaviours displayed by the chlorine-substituted derivatives, a molecular docking study was performed. (C) 2001 Elsevier Science Ltd. All rights reserved.