3,4-dimethoxy-benzoic acid-(4-formyl-phenyl ester) | 26578-71-2

• 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: 3,4-dimethoxy-benzoic acid-(4-formyl-phenyl ester)
• 英文别名: Veratrumsaeure-(4-formyl-phenylester)；4-Veratroyloxy-benzaldehyd；3,4-Dimethoxy-benzoesaeure-(4-formyl-phenylester)；(4-Formylphenyl) 3,4-dimethoxybenzoate
• CAS: 26578-71-2
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: VHAJVSPIIJGINN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 3,4-dimethoxy-benzoic acid-(4-formyl-phenyl ester) 在 potassium permanganate 作用下， 生成 4-[3,4-di(methoxy)benzoyloxy] benzoic acid
  参考文献：
  名称：

  321.一种合成糊精的新方法

  摘要：

  DOI：

  10.1039/jr9320002263
• 作为产物：
  描述：

  藜芦酸 在 氯化亚砜 、 三乙胺 作用下， 生成 3,4-dimethoxy-benzoic acid-(4-formyl-phenyl ester)
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Rhodanine Derivatives as Aldose Reductase Inhibitors

  摘要：

  Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5‐phenylbenzoate containing N‐substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5‐phenylbenzoate moiety deeply influenced the key π‐π stacking while 4‐oxo‐2‐thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs.

  DOI：

  10.1111/cbdd.12369

文献信息

• Design, Synthesis and Evaluation of Rhodanine Derivatives as Aldose Reductase Inhibitors
  作者：Yogesh P. Agrawal、Mona Y. Agrawal、Arun K. Gupta

  DOI：10.1111/cbdd.12369

  日期：2015.2

  Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5‐phenylbenzoate containing N‐substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5‐phenylbenzoate moiety deeply influenced the key π‐π stacking while 4‐oxo‐2‐thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs.
• 321. A new method for the synthesis of depsides
  作者：T. Currie、Alfred Russell

  DOI：10.1039/jr9320002263

  日期：——