3-{4-[(Benzylmethylamino)methyl]phenyl}-6-nitrochromen-2-one | 949580-33-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-{4-[(Benzylmethylamino)methyl]phenyl}-6-nitrochromen-2-one
• 英文别名: 3-[4-[[benzyl(methyl)amino]methyl]phenyl]-6-nitrochromen-2-one
• CAS: 949580-33-0
• 化学式: C₂₄H₂₀N₂O₄
• 分子量: 400.434
• InChiKey: YOADEHMCUGVQME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-{4-[(Benzylmethylamino)methyl]phenyl}-6-nitrochromen-2-one 在 Lindlar's catalyst 氢气 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到6-Amino-3-{4-[(benzylmethylamino)methyl]phenyl}-chromen-2-one
  参考文献：
  名称：

  Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) Derivatives

  摘要：

  AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-beta pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced A beta-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.

  DOI：

  10.1021/jm070100g
• 作为产物：
  描述：

  p-tolylacetic acid sodium salt 在 N-溴代丁二酰亚胺(NBS) 、 乙酸酐 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 27.0h， 生成 3-{4-[(Benzylmethylamino)methyl]phenyl}-6-nitrochromen-2-one
  参考文献：
  名称：

  Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) Derivatives

  摘要：

  AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-beta pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced A beta-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.

  DOI：

  10.1021/jm070100g

文献信息

• Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2<i>H</i>-2-chromenone (AP2238) Derivatives
  作者：Lorna Piazzi、Andrea Cavalli、Federica Belluti、Alessandra Bisi、Silvia Gobbi、Stefano Rizzo、Manuela Bartolini、Vincenza Andrisano、Maurizio Recanatini、Angela Rampa

  DOI：10.1021/jm070100g

  日期：2007.8.1

  AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-beta pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced A beta-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.