5,6-dihydroxy-2-(4-(methyl(propyl)amino)benzylidene)-2,3-dihydro-1H-inden-1-one 4-methylbenzene-1-sulfonic acid | 1402063-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,6-dihydroxy-2-(4-(methyl(propyl)amino)benzylidene)-2,3-dihydro-1H-inden-1-one 4-methylbenzene-1-sulfonic acid
• 英文别名: 5,6-dihydroxy-2-[[4-[methyl(propyl)amino]phenyl]methylidene]-3H-inden-1-one;4-methylbenzenesulfonic acid
• CAS: 1402063-14-2
• 化学式: C₇H₈O₃S*C₂₀H₂₁NO₃
• 分子量: 495.596
• InChiKey: SLIXVIAYMLDAOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  115.14
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5,6-二甲氧基茚酮 在 三溴化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 5,6-dihydroxy-2-(4-(methyl(propyl)amino)benzylidene)-2,3-dihydro-1H-inden-1-one 4-methylbenzene-1-sulfonic acid
  参考文献：
  名称：

  Multitarget-Directed Benzylideneindanone Derivatives: Anti-β-Amyloid (Aβ) Aggregation, Antioxidant, Metal Chelation, and Monoamine Oxidase B (MAO-B) Inhibition Properties against Alzheimer’s Disease

  摘要：

  A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced beta-amyloid (A beta(1-42)) aggregation (10.5-80.1%, 20 mu M) and MAO-B activity (IC50 of 7.5-40.5 mu M), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit A beta(1-42) aggregation (80.1%), and MAO-B (IC50 = 7.5 mu M) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced A beta(1-42) aggregation and disassembling the well-structured A beta fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.

  DOI：

  10.1021/jm300978h

文献信息

• Multitarget-Directed Benzylideneindanone Derivatives: Anti-β-Amyloid (Aβ) Aggregation, Antioxidant, Metal Chelation, and Monoamine Oxidase B (MAO-B) Inhibition Properties against Alzheimer’s Disease
  作者：Ling Huang、Chuanjun Lu、Yang Sun、Fei Mao、Zonghua Luo、Tao Su、Huailei Jiang、Wenjun Shan、Xingshu Li

  DOI：10.1021/jm300978h

  日期：2012.10.11

  A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced beta-amyloid (A beta(1-42)) aggregation (10.5-80.1%, 20 mu M) and MAO-B activity (IC50 of 7.5-40.5 mu M), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit A beta(1-42) aggregation (80.1%), and MAO-B (IC50 = 7.5 mu M) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced A beta(1-42) aggregation and disassembling the well-structured A beta fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.