1-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)-N,N,N-trimethylmethanaminium chloride | 1425441-19-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)-N,N,N-trimethylmethanaminium chloride
• 英文别名: (4,5-Dihydroxy-9,10-dioxoanthracen-2-yl)methyl-trimethylazanium;chloride；(4,5-dihydroxy-9,10-dioxoanthracen-2-yl)methyl-trimethylazanium;chloride
• CAS: 1425441-19-5
• 化学式: C₁₈H₁₈NO₄*Cl
• 分子量: 347.798
• InChiKey: MTTDFIHSJCVZRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 在 氯化亚砜 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)-N,N,N-trimethylmethanaminium chloride
  参考文献：
  名称：

  Design, synthesis and molecular modeling of aloe-emodin derivatives as potent xanthine oxidase inhibitors

  摘要：

  A series of aloe-emodin derivatives were synthesized and evaluated as xanthine oxidase inhibitors. Among them, four aloe-emodin derivatives showed significant inhibitory activities against xanthine oxidase. The compound 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (A1) possessed the best xanthine oxidase inhibitory activity with IC50 of 2.79 mu M. Lineweaver-Burk plot analysis revealed that A1 acted as a mixed-type inhibitor for xanthine oxidase. The docking study revealed that the molecule A1 had strong interactions with the active site of xanthine oxidase and this result was in agreement with kinetic study. Consequently, compound A1 is a new-type candidate for further development for the treatment of gout. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.058

文献信息

• Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors
  作者：Da-Hua Shi、Wei Huang、Chao Li、Ling-Ting Wang、Shi-Fan Wang

  DOI：10.1016/j.bmc.2013.01.015

  日期：2013.3

  A series of aloe-emodin derivatives were designed, synthesized and evaluated as acetylcholinesterase inhibitors. Most of the new prepared compounds showed remarkable acetylcholinesterase inhibitory activities. Among them, the compound 1-((4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl) methyl) pyridin-1-ium chloride (C3) which has a pyridinium substituent possessed the best inhibitory activity

  设计，合成和评估了一系列芦荟大黄素衍生物，作为乙酰胆碱酯酶抑制剂。大多数新制备的化合物显示出显着的乙酰胆碱酯酶抑制活性。其中，具有吡啶鎓取代基的化合物1-（（4,5-二羟基-9,10-二氧杂-9,10-二氢蒽-2-基）甲基）吡啶-1-氯（C3）具有最好的乙酰胆碱酯酶的抑制活性（IC 50  = 0.09μM）。用AUTODOCK进行的对接研究表明C3可以与乙酰胆碱酯酶的催化活性位点（CAS）和外围阴离子位点（PAS）相互作用。