3',4'-(methylenedioxy)phenyl-3,4,5-trimethylgallate | 571923-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3',4'-(methylenedioxy)phenyl-3,4,5-trimethylgallate
• 英文别名: 1,3-Benzodioxol-5-yl 3,4,5-trimethoxybenzoate
• CAS: 571923-85-8
• 化学式: C₁₇H₁₆O₇
• 分子量: 332.31
• InChiKey: VJSWXKWSJQSRFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 氯化亚砜 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3',4'-(methylenedioxy)phenyl-3,4,5-trimethylgallate
  参考文献：
  名称：

  Synthesis, evaluation, and molecular docking studies of cycloalkyl/aryl-3,4,5-trimethylgallates as potent non-ulcerogenic and gastroprotective anti-inflammatory agents

  摘要：

  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.

  DOI：

  10.1007/s00044-013-0620-6

文献信息

• 10.1021/acs.joc.4c00234
  作者：Halder, Pallabi、Mondal, Krishanu、Jash, Arijit、Das, Parthasarathi

  DOI：10.1021/acs.joc.4c00234

  日期：——

  In this study, a ligand-free palladium-catalyzed carbonylation of phenols is conducted under ambient conditions, utilizing the “Chloroform-COware” chemistry. The developed methodology enables the conversion of diverse medicinally relevant phenols, encompassing both natural and synthetic derivatives, into their respective aryl ester counterparts. This transformation is achieved through the reaction with

  在这项研究中，利用“氯仿-COware”化学，在环境条件下进行无配体钯催化的苯酚羰基化。所开发的方法能够将多种药用相关酚（包括天然和合成衍生物）转化为各自的芳基酯对应物。这种转化是通过与广谱芳基和杂芳基碘化物反应实现的。该方案的特点是简单、通用和底物范围广，能够以良好到优异的产率提供生物活性芳基酯衍生物。与导致芳基酯产率较差的一锅法的直接比较凸显了两室装置 (COware) 的卓越效率。此外，我们成功地将这种两室技术应用于克级合成，并将合成的酯后修饰为药学上重要的苯并香豆素核心。
• 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.