3-(4-bromomethylphenyl)-6-methoxychromen-2-one | 949580-75-0

• 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-bromomethylphenyl)-6-methoxychromen-2-one
• CAS: 949580-75-0
• 化学式: C₁₇H₁₃BrO₃
• 分子量: 345.192
• InChiKey: MMLGVCLVOQMJNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-bromomethylphenyl)-6-methoxychromen-2-one 、 N-甲基苄胺 以 甲苯 为溶剂， 反应 15.0h， 生成 3-{4-[(Benzylmethylamino)methyl]phenyl}-6-methoxychromen-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：

  6-methoxy-3-p-tolylchromen-2-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以64%的产率得到3-(4-bromomethylphenyl)-6-methoxychromen-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

• Multi-target-directed coumarin derivatives: hAChE and BACE1 inhibitors as potential anti-Alzheimer compounds
  作者：Lorna Piazzi、Andrea Cavalli、Francesco Colizzi、Federica Belluti、Manuela Bartolini、Francesca Mancini、Maurizio Recanatini、Vincenza Andrisano、Angela Rampa

  DOI：10.1016/j.bmcl.2007.09.100

  日期：2008.1

  The complex etiology of Alzheimer's disease (AD) prompts scientists to develop multifunctional compounds to combat causes and symptoms of such neurodegeneration. To this aim we designed, synthesized, and tested a series of compounds by introducing halophenylalkylamidic functions on the scaffold of AP2238, which is a dual binding site acetylcholinesterase inhibitor. The inhibitory activity was successfully extended to the beta-site amyloid precursor protein cleavage enzyme, leading to the discovery of a potent inhibitor of this enzyme (3) and affording multifunctional compounds (2, 6, 8) for the treatment of AD. (c) 2007 Published by Elsevier Ltd.