N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-(furan-2-ylmethylsulfanyl)acetamide | 108498-90-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-(furan-2-ylmethylsulfanyl)acetamide
• CAS: 108498-90-4
• 化学式: C₁₇H₂₄N₂O₃S₂
• 分子量: 368.521
• InChiKey: UQPFDBQMUHZUOU-UHFFFAOYSA-N

物化性质

• 沸点：
  521.6±50.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-二甲基氯烯亚胺 、 N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-(furan-2-ylmethylsulfanyl)acetamide 以 乙腈 为溶剂， 反应 72.0h， 以75%的产率得到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
• 作为产物：
  描述：

  2-<(2-furanylmethyl)thio>acetyl chloride 、 2-(((5-二甲基氨基)甲基)-2-呋喃基)甲基)硫代乙胺 以 乙腈 为溶剂， 反应 24.0h， 以58%的产率得到N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-(furan-2-ylmethylsulfanyl)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

文献信息

• A Novel Histamine 2(H2) Receptor Antagonist with Gastroprotective Activity. II. Synthesis and Pharmacological Evaluation of 2-Furfuryl-thio and 2-Furfurylsulfinyl Acetamide Derivatives with Heteroaromatic Rings.
  作者：Nobuhiko HIRAKAWA、Hajime MATSUMOTO、Akihiko HOSODA、Akihiro SEKINE、Tetsuaki YAMAURA、Yasuo SEKINE

  DOI：10.1248/cpb.46.616

  日期：——

  recently found that N-[3-[3-(piperidinomethyl)phenoxyl]propyl]acetamide derivatives with a thioether function showed gastric anti-secretory and gastroprotective activities and that the thioether function (particularly furfurylthio or furfurylsulfinyl) was essential for gastroprotection. In the present study, a series of 2-furfurylthio and 2-furfurylsulfinyl acetamide derivatives were synthesized and

  我们最近发现具有硫醚功能的N- [3- [3-（3-哌啶基甲基）苯氧基]丙基]乙酰胺衍生物具有抗胃分泌和保护胃的活性，硫醚功能（尤其是糠基硫基或糠基亚磺酰基）对于胃保护至关重要。在本研究中，合成了一系列2-糠基硫基和2-糠基亚磺酰基乙酰胺衍生物，并评估了其对组胺H2受体的拮抗活性，胃的抗分泌活性和胃保护作用。根据N- [3- [3-（哌啶子基甲基）苯氧基]丙基]乙酰胺的结构，设计了其中3-（哌啶子基甲基）苯氧基部分被连接到叔胺上的多种杂芳族环取代的化合物。丙基被其他碳键取代。讨论了构效关系。在测试的化合物中，2-糠基亚磺酰基-N- [4- [4-（哌啶子基甲基）-2-吡啶基氧基γ]-（Z）-2-丁烯基]乙酰胺是最有效的，其代号为FRG-8813。
• SEKINE, YASUO;HIRAKAWA, NOBUHIRO;KASHIWABA, NORIAKI;YAMAURA, TETSUAKI;HAR+
  作者：SEKINE, YASUO、HIRAKAWA, NOBUHIRO、KASHIWABA, NORIAKI、YAMAURA, TETSUAKI、HAR+

  DOI：——

  日期：——
• Synthesis and cholinergic properties of bis[[(dimethylamino)methyl]furanyl] analogs of ranitidine
  作者：J. Walter Sowell、Yunzhao Tang、Matthew J. Valli、James M. Chapman、Laura A. Usher、Celeste M. Vaughan、J. W. Kosh

  DOI：10.1021/jm00084a015

  日期：1992.3

  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.