2-acetylthiomethyl-4-(4-chlorophenyl)-4-oxobutanoic acid | 101973-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetylthiomethyl-4-(4-chlorophenyl)-4-oxobutanoic acid
• 英文别名: 2-acetylthiomethyl-3-(4-chlorobenzoyl)propionic acid；2-(acetylsulfanylmethyl)-4-(4-chlorophenyl)-4-oxobutanoic acid
• CAS: 101973-75-5
• 化学式: C₁₃H₁₃ClO₄S
• 分子量: 300.763
• InChiKey: QABORLAFISHFKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-acetylthiomethyl-4-(4-chlorophenyl)-4-oxobutanoic acid 在 氢氧化钾 、 硫酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 10.5h， 生成 2-(4-chlorophenyl)thiophene-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009
• 作为产物：
  描述：

  硫代乙酸 生成 2-acetylthiomethyl-4-(4-chlorophenyl)-4-oxobutanoic acid
  参考文献：
  名称：

  TOMIDZAVA, KADZUYUKI;KAMEHO, KADZUYA;MATSUNAGA, AKIRA;SAJTO, XIDEHDZI;MAS+

  摘要：

  DOI：

文献信息

• Studies on antirheumatic agents. 3-Benzoylpropionic acid derivatives.
  作者：KAZUYA KAMEO、KUNIO OGAWA、KIMIYO TAKESHITA、SHIRO NAKAIKE、KAZUYUKI TOMISAWA、KAORU SOTA

  DOI：10.1248/cpb.36.2050

  日期：——

  As part of the search for new antirheumatic agents, three types of 3-benzoylpropionic acid derivatives having a mercapto moiety in their structures were prepared, and tested for suppressing activity on adjuvant arthritis in Sprague-Dawley rats. A structure-activity relationship study showed that substitution on the phenyl ring contributed to the activity and the most favorable substituent was different in each type of derivative.

  作为寻找新型抗风湿药物的一部分，制备了三种含有巯基结构单元的3-苯甲酰丙酸衍生物，并测试了它们对Sprague-Dawley大鼠佐剂性关节炎的抑制活性。结构-活性关系研究表明，苯环上的取代基对活性有贡献，且每种衍生物中最有利的取代基各不相同。
• ——
  作者：TOMISAWA KAZUYUKI、 KAMEO KAZUYA、 MATSUNAGA TORU、 SATO SHIUJI、 SOTA KAORU

  DOI：——

  日期：——
• KAMEO, KAZUYA;OGAWA, KUNIO;TAKESHITA, KIMIYO;NAKAIKE, SHIRO;TOMISAWA, KAZ+, CHEM. AND PHARM. BULL., 36,(1988) N 6, C. 2050-2060
  作者：KAMEO, KAZUYA、OGAWA, KUNIO、TAKESHITA, KIMIYO、NAKAIKE, SHIRO、TOMISAWA, KAZ+

  DOI：——

  日期：——