2-<(2-furanylmethyl)thio>acetyl chloride | 89793-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-<(2-furanylmethyl)thio>acetyl chloride
• 英文别名: furfurylsulfanyl-acetyl chloride；α-Furfurylmercapto-essigsaeurechlorid；{[(Furan-2-yl)methyl]sulfanyl}acetyl chloride；2-(furan-2-ylmethylsulfanyl)acetyl chloride
• CAS: 89793-50-0
• 化学式: C₇H₇ClO₂S
• 分子量: 190.65
• InChiKey: RMJLLURIJLDVAS-UHFFFAOYSA-N

物化性质

• 沸点：
  241.4±25.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(2-furanylmethyl)thio>acetyl chloride 以 乙腈 为溶剂， 反应 96.0h， 生成 2-(5-Dimethylaminomethyl-furan-2-ylmethylsulfanyl)-N-[2-(5-dimethylaminomethyl-furan-2-ylmethylsulfanyl)-ethyl]-acetamide
  参考文献：
  名称：

  Synthesis and cholinergic properties of bis[[(dimethylamino)methyl]furanyl] analogs of ranitidine

  摘要：

  The histaminergic H-2 antagonist, ranitidine, has also been found to significantly inhibit acetylcholinesterase (AChE) in vitro. In an effort to develop novel, nonquaternary AChE inhibitors capable of penetrating into the CNS and alleviating the cholinergic deficit characteristic of Alzheimer's disease, a series of bis[[(dimethylamino)methyl]furanyl] analogues of ranitidine has been synthesized. All compounds were evaluated for human erythrocyte AChE inhibitory activity and compared to ranitidine, physostigmine, and tetrahydro-9-aminoacridine (THA). The most active AChE inhibitors were N,N'-disubstituted derivatives of 2-nitro-1,1-ethenediamine and 4,6-dinitro-1,3-benzenediamine, with compound 8 demonstrating activity greater than physostigmine. Deletion of the diaminonitroethene group in a series of alkyl and aryl bis-thioethers, yielded a number of slightly less active compounds, comparable in potency to THA. The 13 most active AChE inhibitors all demonstrated a more selective inhibition of AChE, as opposed to butyrylcholinesterase inhibition, than did THA. Compounds 3 and 22 were equally active to THA in potentiating rat ileal contractions. Binding studies demonstrated M1 and M2 cholinergic receptor affinities slightly greater than or equal to THA. Differential receptor binding studies showed compound 12 resembled THA in agonist/antagonist activity. Compounds 11-13 significantly elevated mouse brain acetylcholine levels, when administered at 80% of their approximate lethal doses, but were less active than THA or physostigmine.

  DOI：

  10.1021/jm00084a015