5-(4-Chloro-phenyl)-2,3-dihydro-thiophene-3-carboxylic acid methyl ester | 130655-93-5

• 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: 5-(4-Chloro-phenyl)-2,3-dihydro-thiophene-3-carboxylic acid methyl ester
• CAS: 130655-93-5
• 化学式: C₁₂H₁₁ClO₂S
• 分子量: 254.737
• InChiKey: NCNDBKJUHMFGJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  5-(4-Chloro-phenyl)-2,3-dihydro-thiophene-3-carboxylic acid methyl ester 在 六甲基磷酰三胺 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 、 sodium 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 10.0h， 生成 Methyl 3-[5-(4-chlorophenyl)thiophen-3-yl]propanoate
  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：

  甲醇 、 2-acetylthiomethyl-4-(4-chlorophenyl)-4-oxobutanoic acid 在 硫酸 作用下， 反应 5.0h， 生成 5-(4-Chloro-phenyl)-2,3-dihydro-thiophene-3-carboxylic acid methyl ester
  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