4,5-bis(allyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,5-bis(allyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
• 英文别名: 9,10-Dioxo-4,5-bis(prop-2-enoxy)anthracene-2-carbaldehyde；9,10-dioxo-4,5-bis(prop-2-enoxy)anthracene-2-carbaldehyde
• 化学式: C₂₁H₁₆O₅
• 分子量: 348.355
• InChiKey: FUKFIWUBCVWRSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-bis(allyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 、 O-乙基羟胺 以 1,4-二氧六环 、 乙醇 为溶剂， 以71%的产率得到4,5-bis(allyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde O-ethyl oxime
  参考文献：
  名称：

  Design and synthesis of aloe-emodin derivatives as potent anti-tyrosinase, antibacterial and anti-inflammatory agents

  摘要：

  Twenty aloe-emodin derivatives were designed, synthesized, and their biological activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, compounds with thiosemicarbazide moiety showed more potent inhibitory effects than the other compounds. The structure-activity relationships (SARs) were preliminarily discussed. The inhibition mechanism of selected compounds 1 and 13 were investigated. The results showed compound 1 was reversible inhibitor, however, compound 13 was irreversible. Kinetic analysis indicated that compound 1 was competitive tyrosinase inhibitor. Furthermore, the antibacterial activities and anti-inflammatory activities of some selected compounds were also screened. The results showed that compound 3 exhibited more potent antibacterial activity than the aloe-emodin, compounds 5 and 6 possessed more potent anti-inflammatory activities than the diacerein. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.004
• 作为产物：
  描述：

  芦荟大黄素 在 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 44.0h， 生成 4,5-bis(allyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
  参考文献：
  名称：

  Design and synthesis of aloe-emodin derivatives as potent anti-tyrosinase, antibacterial and anti-inflammatory agents

  摘要：

  Twenty aloe-emodin derivatives were designed, synthesized, and their biological activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, compounds with thiosemicarbazide moiety showed more potent inhibitory effects than the other compounds. The structure-activity relationships (SARs) were preliminarily discussed. The inhibition mechanism of selected compounds 1 and 13 were investigated. The results showed compound 1 was reversible inhibitor, however, compound 13 was irreversible. Kinetic analysis indicated that compound 1 was competitive tyrosinase inhibitor. Furthermore, the antibacterial activities and anti-inflammatory activities of some selected compounds were also screened. The results showed that compound 3 exhibited more potent antibacterial activity than the aloe-emodin, compounds 5 and 6 possessed more potent anti-inflammatory activities than the diacerein. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.004