5'-methyl-2'-(1''-methylethyl)phenyl-3,4,5-trimethylgallate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 5'-methyl-2'-(1''-methylethyl)phenyl-3,4,5-trimethylgallate
• 英文别名: 5-methyl-2-(methylethyl)phenyl 3,4,5-trimethoxybenzoate；2-Isopropyl-5-methylphenyl 3,4,5-trimethoxybenzoate；(5-methyl-2-propan-2-ylphenyl) 3,4,5-trimethoxybenzoate
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: NEFINPNMAWNQLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸甲酯 在 吡啶 、 氢氧化钾 作用下， 生成 5'-methyl-2'-(1''-methylethyl)phenyl-3,4,5-trimethylgallate
  参考文献：
  名称：

  Depigmenting Activity and Low Cytotoxicity of Alkoxy Benzoates or Alkoxy Cinnamte in Cultured Melanocytes

  摘要：

  为了获得有效且安全的局部脱色剂，我们合成了含百里酚基团的羟基苯甲酸盐、烷氧基苯甲酸盐和3,4,5-三甲氧基肉桂酸盐，并对其在培养的黑素细胞中抑制黑色素合成的高水平活性进行了筛选。我们使用小鼠黑素细胞系测试了八种化合物的脱色效果和细胞毒性。研究发现，通过将3,4,5-三烷氧基苯甲酸和3,4,5-三甲氧基肉桂酸与百里酚结合合成的3,4,5-三烷氧基苯甲酸盐和3,4,5-三甲氧基肉桂酸盐显示出强大的脱色效果和低细胞毒性。化合物4h，5-甲基-2-（甲基乙基）苯基（2E）-3-（3,4,5-三甲氧基苯基）丙-2-烯酸酯，显示出最强的脱色效果（IC50=10 μM）和低细胞毒性（IC50=200 μM）。

  DOI：

  10.1248/cpb.51.1085

文献信息

• Synthesis, evaluation, and molecular docking studies of cycloalkyl/aryl-3,4,5-trimethylgallates as potent non-ulcerogenic and gastroprotective anti-inflammatory agents
  作者：Mamta Sachdeva Dhingra、Pran Kishore Deb、Renu Chadha、Tejvir Singh、Maninder Karan

  DOI：10.1007/s00044-013-0620-6

  日期：2014.1

  In our effort to identify the effective gastric sparing and protective anti-inflammatory agents, a series of cycloalkyl/aryl-3,4,5-trimethylgallates were synthesized and characterized. The physicochemical properties were studied to assess the lipophilicity and chemical stability. Subsequently, the compounds were evaluated for their anti-inflammatory activity and effect on gastric mucosa by most active compounds. All the compounds exhibited promising anti-inflammatory activity. In particular, 4a, 4b, 4g, and 4h emerged as the most active compounds in the series. The results of gastric mucosal studies and biochemical estimations suggested that these compounds are non-ulcerogenic and gastroprotective. The molecular docking analysis was performed to understand the binding interactions of these compounds to cyclooxygenase isoenzyme (COX-1 and COX-2). The results from this investigation suggests cycloalkyl/aryl-3,4,5-trimethylgallates as potent safer gastrosparing and protective anti-inflammatory agents.