4-[(benzylmethylamino)methyl]benzaldehyde | 1224099-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(benzylmethylamino)methyl]benzaldehyde
• 英文别名: 4-[[Benzyl(methyl)amino]methyl]benzaldehyde
• CAS: 1224099-40-4
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: QQQBGQKBWFYJSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(benzylmethylamino)methyl]benzaldehyde 、 6-(7-bromoheptyloxy)indan-1-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以55%的产率得到2-{4-[(benzylmethylamino)methyl]benzylidene}-6-(7-bromoheptyloxy)indan-1-one
  参考文献：
  名称：

  Targeting Alzheimer’s disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238

  摘要：

  We report on a series of hybrid compounds structurally derived from donepezil and AP2238. This study was aimed at improving the activities of the reference compounds, donepezil and AP2238, and at broadening the range of activities of new derivatives as, due to the multifactorial nature of AD, molecules that modulate the activity of a single protein target are unable to significantly modify the progression of the disease. In particular, the indanone core from donepezil was linked to the phenyl-N-methylbenzylamino moiety from AP2238, through a double bond that was kept to evaluate the role of a lower flexibility in the biological activities. Moreover, SAR studies were performed to evaluate the role of different substituents in position 5 or 6 of the indanone ring in the interaction with the PAS, introducing also alkyl chains of different lengths carrying different amines at one end. Derivatives 21 and 22 proved to be the most active within the series and their potencies against AChE were in the same order of magnitude of the reference compounds. Compounds 15, 21-22, with a 5-carbon alkyl chain bearing an amino moiety at one end, better contacting the PAS, remarkably improved the inhibition of AChE-induced A beta aggregation with respect to the reference compounds. They also showed activity against self-aggregation of A beta(42) peptide, the most amyloidogenic form of amyloid produced in AD brains, while the reference compounds resulted completely ineffective. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.071
• 作为产物：
  描述：

  4-溴甲基苯甲酸甲酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-[(benzylmethylamino)methyl]benzaldehyde
  参考文献：
  名称：

  具有 AChE 和 MAO-B 双重抑制活性的新型 E/Z 2-Benzylideneindan-1-One 光开关的研究

  摘要：

  与更传统的“一种疾病一目标一药物”相反，多靶点治疗策略可能有望治疗多因素神经退行性综合征，例如阿尔茨海默病（AD）和相关痴呆症。最近，我们将光药理学方法与多靶点定向配体（MTDL）设计策略相结合，公开了一种新型多奈哌齐类化合物，即2-(4-((二乙氨基)甲基)亚苄基)-5-甲氧基-2,3-二氢-1H-茚-1-酮 (1a)，其 E 异构体形式（UV-B 光诱导异构体 Z 的含量低约十倍）显示出作为 AD 相关靶点乙酰胆碱酯酶双重抑制剂的最佳活性。 AChE) 和单胺氧化酶 B (MAO-B)。在此，我们进一步研究了具有不同体积和亲脂性烷基的非共轭叔氨基部分的可光致异构化的2-亚苄基茚满-1-酮类似物1b-h。对于每种化合物，研究了热稳定的 E 几何异构体以及在光稳态（PSS，75% Z）下通过 UV-B 光照射产生的 E/Z 混合物对人 ChE 和 MAO 的抑制作用。N-苄基（乙基）氨基类似物的纯

  DOI：

  10.3390/molecules28155857

文献信息

• US5656644A
  申请人：——

  公开号：US5656644A

  公开（公告）日：1997-08-12
• US5916891A
  申请人：——

  公开号：US5916891A

  公开（公告）日：1999-06-29