(2Z)-2-(4-methoxy-3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (2Z)-2-(4-methoxy-3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (2Z)-2-[(4-methoxy-3-nitrophenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: XTCVGBSMOYQFLG-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-茚酮 、 3-硝基-4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以54.1%的产率得到(2Z)-2-(4-methoxy-3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Inhibitory kinetics of novel 2,3-dihydro-1 H -inden-1-one chalcone-like derivatives on mushroom tyrosinase

  摘要：

  In this study, novel 2,3-dihydro-1H-inden-1-one chalcone-like compounds and their hydroxyl derivatives were synthesized, and their inhibitory effects on mushroom tyrosinase activity were evaluated. Two of the compounds synthesized inhibited the diphenolase activity of tyrosinase in a dose dependent manner and exhibited much higher tyrosinase inhibitory activities (IC50 values of 12.3 mu M and 8.2 mu M, respectively) than the positive control, kojic acid (IC50: 27.5 mu M). Kinetic analysis showed that their inhibition was reversible. Both the novel compounds displayed competitive inhibition with their K-i values of 10.3 mu M and 8.7 mu M, respectively. This study suggests hydroxy substituted 2,3-dihydro-1H-inden-1-one chalcone-like compounds to serve as promising candidates for use as depigmentation agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.071

文献信息

• Inhibitory kinetics of novel 2,3-dihydro-1 H -inden-1-one chalcone-like derivatives on mushroom tyrosinase
  作者：Sini Radhakrishnan、Ronald Shimmon、Costa Conn、Anthony Baker

  DOI：10.1016/j.bmcl.2015.10.071

  日期：2015.12

  In this study, novel 2,3-dihydro-1H-inden-1-one chalcone-like compounds and their hydroxyl derivatives were synthesized, and their inhibitory effects on mushroom tyrosinase activity were evaluated. Two of the compounds synthesized inhibited the diphenolase activity of tyrosinase in a dose dependent manner and exhibited much higher tyrosinase inhibitory activities (IC50 values of 12.3 mu M and 8.2 mu M, respectively) than the positive control, kojic acid (IC50: 27.5 mu M). Kinetic analysis showed that their inhibition was reversible. Both the novel compounds displayed competitive inhibition with their K-i values of 10.3 mu M and 8.7 mu M, respectively. This study suggests hydroxy substituted 2,3-dihydro-1H-inden-1-one chalcone-like compounds to serve as promising candidates for use as depigmentation agents. (C) 2015 Elsevier Ltd. All rights reserved.