4-(4-acetyloxymethylphenyl)-2-acetylthiomethyl-4-oxobutanoic acid | 485817-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-acetyloxymethylphenyl)-2-acetylthiomethyl-4-oxobutanoic acid
• 英文别名: 4-(4-acetoxymethylphenyl)-2-acetylthiomethyl-4-oxobutanoic acid；4-[4-(Acetyloxymethyl)phenyl]-2-(acetylsulfanylmethyl)-4-oxobutanoic acid；4-[4-(acetyloxymethyl)phenyl]-2-(acetylsulfanylmethyl)-4-oxobutanoic acid
• CAS: 485817-70-7
• 化学式: C₁₆H₁₈O₆S
• 分子量: 338.381
• InChiKey: WFOSHKZZKZPJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-acetyloxymethylphenyl)-2-acetylthiomethyl-4-oxobutanoic acid 在 ammonium hydroxide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (+/-)-4-(4-hydroxymethylphenyl)-2-methylsulfinylmethyl-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and Antirheumatic Activity of the Metabolites of Esonarimod

  摘要：

  We have developed esonarimod, (+/-)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, as a new antirheumatic drug. Now we describe herein the preparation of the enantiomers of (+/-)-deacetylesonarimod, the pharmaceutically active metabolites of esonarimod, and comparison of their antirheumatic activities. No significant difference has been observed between the two enantiomers. In a pre-clinical study of esonarimod, other metabolites were detected in rat blood or urine. We also synthesized these compounds as authentic samples to analyze the human metabolites in clinical studies of esonarimod. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00084-6
• 作为产物：
  描述：

  4-(羟基甲基)苯甲醛乙酸二乙酯 在 吡啶 、 indium 、 jones reagent 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 丙酮 、 甲苯 为溶剂， 反应 3.25h， 生成 4-(4-acetyloxymethylphenyl)-2-acetylthiomethyl-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and Antirheumatic Activity of the Metabolites of Esonarimod

  摘要：

  We have developed esonarimod, (+/-)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, as a new antirheumatic drug. Now we describe herein the preparation of the enantiomers of (+/-)-deacetylesonarimod, the pharmaceutically active metabolites of esonarimod, and comparison of their antirheumatic activities. No significant difference has been observed between the two enantiomers. In a pre-clinical study of esonarimod, other metabolites were detected in rat blood or urine. We also synthesized these compounds as authentic samples to analyze the human metabolites in clinical studies of esonarimod. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00084-6

文献信息

• Noguchi, Toshiya; Onodera, Akira; Tomisawa, Kazuyuki, Heterocycles, 2002, vol. 57, # 10, p. 1907 - 1914
  作者：Noguchi, Toshiya、Onodera, Akira、Tomisawa, Kazuyuki、Yokomori, Sadakazu

  DOI：——

  日期：——
• Synthesis and Antirheumatic Activity of the Metabolites of Esonarimod
  作者：Toshiya Noguchi、Akira Onodera、Kazuyuki Tomisawa、Miyuki Yamashita、Kimiyo Takeshita、Sadakazu Yokomori

  DOI：10.1016/s0968-0896(02)00084-6

  日期：2002.8

  We have developed esonarimod, (+/-)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, as a new antirheumatic drug. Now we describe herein the preparation of the enantiomers of (+/-)-deacetylesonarimod, the pharmaceutically active metabolites of esonarimod, and comparison of their antirheumatic activities. No significant difference has been observed between the two enantiomers. In a pre-clinical study of esonarimod, other metabolites were detected in rat blood or urine. We also synthesized these compounds as authentic samples to analyze the human metabolites in clinical studies of esonarimod. (C) 2002 Elsevier Science Ltd. All rights reserved.