(2Z)-2-(2,4-dimethoxybenzylidene)-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-(2,4-dimethoxybenzylidene)-2, 3-dihydro-1H-inden-1-one
• 英文别名: 2-(2,4-dimethoxy-benzylidene)-indan-1-one；2-(2,4-Dimethoxy-benzyliden)-indan-1-on；(2Z)-2-[(2,4-dimethoxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: ZFNBHDZFYPETHF-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(2,4-dimethoxybenzylidene)-2, 3-dihydro-1H-inden-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以51.2%的产率得到(2Z)-2-(2,4-dihydroxybenzylidene)-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
• 作为产物：
  描述：

  1-茚酮 、 2,4-二甲氧基苯甲醛 在 potassium carbonate 作用下， 生成 (2Z)-2-(2,4-dimethoxybenzylidene)-2, 3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Perkin; Robinson, Journal of the Chemical Society, 1907, vol. 91, p. 1102

  摘要：

  DOI：

文献信息

• Perkin; Robinson, Journal of the Chemical Society, 1907, vol. 91, p. 1102
  作者：Perkin、Robinson

  DOI：——

  日期：——
• 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.