N-[2-[[5-(二甲基氨基甲基)呋喃-2-基]甲硫基]乙基]-5-氟-2,4-二硝基苯胺 | 142744-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[2-[[5-(二甲基氨基甲基)呋喃-2-基]甲硫基]乙基]-5-氟-2,4-二硝基苯胺
• 中文别名: 吡啶,2-(4-甲基-2-羟基-1,2,3-氧杂噻唑烷-3-基)-,(4R)-(9CI)
• 英文名称: N-<2-<<<5-<(dimethylamino)methyl>-2-furanyl>methyl>thio>ethyl>-2,4-dinitro-5-fluoroaniline
• 英文别名: N-(2-(((5-((Dimethylamino)methyl)-2-furanyl)methyl)thio)ethyl)-2,4-dinitro-5-fluoroaniline；N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-5-fluoro-2,4-dinitroaniline
• CAS: 142744-14-7
• 化学式: C₁₆H₁₉FN₄O₅S
• 分子量: 398.415
• InChiKey: LAFTTYMJFZRMQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[2-[[5-(二甲基氨基甲基)呋喃-2-基]甲硫基]乙基]-5-氟-2,4-二硝基苯胺 在 氨 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 以95%的产率得到N'-[2-[[5-(二甲基氨基甲基)呋喃-2-基]甲硫基]乙基]-4,6-二硝基苯-1,3-二胺
  参考文献：
  名称：

  Synthesis and cholinergic properties of N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamino analogs of ranitidine

  摘要：

  A series of N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamino analogs of the H-2-antagonist, ranitidine, was synthesized and the abilities of the compounds to alleviate the cholinergic deficit characteristic of Alzheimer's disease evaluated. The compounds were initially tested for their ability to inhibit human erythrocyte acetylcholinesterase activity in vitro. Selected compounds were further evaluated for butyrylcholinesterase inhibition, M1 and M2 cholinergic receptor binding, potentiation of ileal contractions, and the ability to elevate brain acetylcholine levels in mice. The analogs were compared to tetrahydroaminoacridine and to a recently reported series of bis-[[(dimethylamino)methyl]furans]. The N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamine derivatives were generally comparable to tetrahydroaminoacridine and the bis[ [(dimethylamino)methyl]furans] in acetylcholinesterase inhibition, M1/M2 receptor binding, and the potentiation of ileal contractions, while being more potent inhibitors of acetylcholinesterase than butyrylcholinesterase. The 4-nitro-3-pyridazinyl analog, 26, was notable in demonstrating a potent and selective binding to the M2 receptor, with an M2 IC50/M1 IC50 of 0.060. Compounds in which the substituents on the dinitro-N-aryl moiety were relatively small were the best at inhibiting acetylcholinesterase in vitro. The N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thiolethylamines in general, and those with small N-aryl substituents in particular, were superior to the bis[[(dimethylamino)methyl]furans] in elevating brain ACh levels in mice, probably due to enhanced distribution into the CNS. The 1,5-difluoro-2,4-dinitrophenyl analog, 8, resulted in the largest elevation in brain acetylcholine levels, affording a 53% increase at 88 mg/kg.

  DOI：

  10.1021/jm00095a008
• 作为产物：
  描述：

  1,5-二氟-2,4-二硝基苯 、 2-(((5-二甲基氨基)甲基)-2-呋喃基)甲基)硫代乙胺 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以90%的产率得到N-[2-[[5-(二甲基氨基甲基)呋喃-2-基]甲硫基]乙基]-5-氟-2,4-二硝基苯胺
  参考文献：
  名称：

  Synthesis and cholinergic properties of N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamino analogs of ranitidine

  摘要：

  A series of N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamino analogs of the H-2-antagonist, ranitidine, was synthesized and the abilities of the compounds to alleviate the cholinergic deficit characteristic of Alzheimer's disease evaluated. The compounds were initially tested for their ability to inhibit human erythrocyte acetylcholinesterase activity in vitro. Selected compounds were further evaluated for butyrylcholinesterase inhibition, M1 and M2 cholinergic receptor binding, potentiation of ileal contractions, and the ability to elevate brain acetylcholine levels in mice. The analogs were compared to tetrahydroaminoacridine and to a recently reported series of bis-[[(dimethylamino)methyl]furans]. The N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamine derivatives were generally comparable to tetrahydroaminoacridine and the bis[ [(dimethylamino)methyl]furans] in acetylcholinesterase inhibition, M1/M2 receptor binding, and the potentiation of ileal contractions, while being more potent inhibitors of acetylcholinesterase than butyrylcholinesterase. The 4-nitro-3-pyridazinyl analog, 26, was notable in demonstrating a potent and selective binding to the M2 receptor, with an M2 IC50/M1 IC50 of 0.060. Compounds in which the substituents on the dinitro-N-aryl moiety were relatively small were the best at inhibiting acetylcholinesterase in vitro. The N-aryl-2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thiolethylamines in general, and those with small N-aryl substituents in particular, were superior to the bis[[(dimethylamino)methyl]furans] in elevating brain ACh levels in mice, probably due to enhanced distribution into the CNS. The 1,5-difluoro-2,4-dinitrophenyl analog, 8, resulted in the largest elevation in brain acetylcholine levels, affording a 53% increase at 88 mg/kg.

  DOI：

  10.1021/jm00095a008