3-噻吩丙酸,5-苯基-,乙基酯 | 194142-11-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-噻吩丙酸,5-苯基-,乙基酯
• 英文名称: ethyl 3-(5-phenylthiophen-3-yl)propanoate
• CAS: 194142-11-5
• 化学式: C₁₅H₁₆O₂S
• 分子量: 260.357
• InChiKey: QFVWTJHPILOQOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-噻吩丙酸,5-苯基-,乙基酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以62%的产率得到3-(5-Phenylthiophen-3-yl)propanoic 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：

  4-Chloromethyl-2-phenyl-thiophene 在 sodium 、 sodium chloride 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 3-噻吩丙酸,5-苯基-,乙基酯
  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