3-Hydroxymethyl-4,6-dimethoxy-2,5-dimethyl-benzoic acid methyl ester | 148014-53-3

• 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-Hydroxymethyl-4,6-dimethoxy-2,5-dimethyl-benzoic acid methyl ester
• 英文别名: Methyl 5-(hydroxymethyl)-2,4-dimethoxy-3,6-dimethylbenzoate
• CAS: 148014-53-3
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: AVANKXQAACLXDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Hydroxymethyl-4,6-dimethoxy-2,5-dimethyl-benzoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 2.25h， 生成 Methyl 5-[(2,4-dimethoxy-5-methoxycarbonyl-3,6-dimethylphenyl)methyl]-2,4-dimethoxy-3,6-dimethylbenzoate
  参考文献：
  名称：

  Synthesis and Phospholipase A₂ Inhibitory Activity of Thielocin B3 Derivatives

  摘要：

  We prepared several types of derivatives of thielocin B3, a very potent naturally occurring inhibitor for human nonpancreatic secretory PLA(2) (sPLA(2)-II), and conducted a structure-activity relationship study to identify potent sPLA(2)-II inhibitors with the aim of developing antiinflammatory drugs. The total number of aromatic rings is critical for sPLA(2)-II inhibition, and the best result was obtained in the case of six rings. The structure of the central part of the inhibitors was not specific, and potent inhibitors were found among the sulfide, sulfone, ether, methylene, and amino derivatives. Although a diester of the terminal carboxylic acid lost its inhibitory activity, having both of the carboxylic acids was not necessary for expression of activity, as illustrated by a glycine derivative with the benzyl ester group 36. Among the newly synthesized derivatives, 18, 20, 29, and 36 showed very potent human sPLA(2)-II inhibitory activity comparable to that of natural thielocin B3. Their IC50 values are in the range 0.069-0.14 mu M, and they are a class of compounds showing the most potent sPLA(2)-II inhibition to date.

  DOI：

  10.1021/jm960437a
• 作为产物：
  描述：

  formyl-3-dimethoxy-4,6-dimethyl-2,5-benzoate de methyle 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 以3.18 g的产率得到3-Hydroxymethyl-4,6-dimethoxy-2,5-dimethyl-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis and Phospholipase A₂ Inhibitory Activity of Thielocin B3 Derivatives

  摘要：

  We prepared several types of derivatives of thielocin B3, a very potent naturally occurring inhibitor for human nonpancreatic secretory PLA(2) (sPLA(2)-II), and conducted a structure-activity relationship study to identify potent sPLA(2)-II inhibitors with the aim of developing antiinflammatory drugs. The total number of aromatic rings is critical for sPLA(2)-II inhibition, and the best result was obtained in the case of six rings. The structure of the central part of the inhibitors was not specific, and potent inhibitors were found among the sulfide, sulfone, ether, methylene, and amino derivatives. Although a diester of the terminal carboxylic acid lost its inhibitory activity, having both of the carboxylic acids was not necessary for expression of activity, as illustrated by a glycine derivative with the benzyl ester group 36. Among the newly synthesized derivatives, 18, 20, 29, and 36 showed very potent human sPLA(2)-II inhibitory activity comparable to that of natural thielocin B3. Their IC50 values are in the range 0.069-0.14 mu M, and they are a class of compounds showing the most potent sPLA(2)-II inhibition to date.

  DOI：

  10.1021/jm960437a