2-(5-(4-chlorophenyl)thiophen-2-yl)acetic acid | 24680-42-0

• 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: 2-(5-(4-chlorophenyl)thiophen-2-yl)acetic acid
• 英文别名: 2-[5-(4-Chlorophenyl)thiophen-2-yl]acetic acid
• CAS: 24680-42-0
• 化学式: C₁₂H₉ClO₂S
• 分子量: 252.721
• InChiKey: QLNOZUXAMSOBQH-UHFFFAOYSA-N

物化性质

• 沸点：
  405.1±35.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(5-(4-chlorophenyl)thiophen-2-yl)acetic acid 在 硫酸 作用下， 以67%的产率得到[5-(4-Chloro-phenyl)-thiophen-2-yl]-acetic 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
• 作为产物：
  描述：

  2-(Chloromethyl)-5-(4-chlorophenyl)thiophene 在 氢氧化钾 、 18-冠醚-6 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 2-(5-(4-chlorophenyl)thiophen-2-yl)acetic 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

文献信息

• [EN] NOVEL THIOPHENE COMPOUNDS, PROCESS FOR SYNTHESIS AND USE THEREOF<br/>[FR] NOUVEAUX COMPOSÉS DE THIOPHÈNE, PROCÉDÉ DE SYNTHÈSE ET D'UTILISATION DE CEUX-CI
  申请人：AHAMMUNE BIOSCIENCES PRIVATE LTD

  公开号：WO2019043642A1

  公开（公告）日：2019-03-07

  The present invention relates to novel thiophene compounds of general Formula I, and their stereoisomers (diastereoisomers, enantiomers), pure or mixed, racemic mixtures, geometrical isomers, tautomers, pharmaceutically acceptable salts, hydrates, solvates, solid forms and mixtures thereof along with process for their preparation. The present invention discloses compounds that are useful in the treatment and prevention of autoimmune diseases.

  本发明涉及一般式I的新型噻吩化合物，以及它们的立体异构体（顺反异构体、对映异构体），纯或混合、外消旋混合物、几何异构体、互变异构体、药学上可接受的盐、水合物、溶剂合物、固体形式及其混合物，以及用于它们的制备的方法。本发明揭示了在治疗和预防自身免疫疾病中有用的化合物。
• BEATON C. M.; CHAPMAN N. B.; CLARKE K.; WILLIS J. M., J. CHEM. SOC. PERKIN TRANS., PART 1 <JCPK-BH>, 1976, NO 22, 2355-2363
  作者：BEATON C. M.、 CHAPMAN N. B.、 CLARKE K.、 WILLIS J. M.

  DOI：——

  日期：——
• NOVEL THIOPHENE COMPOUNDS, PROCESS FOR SYNTHESIS AND USE THEREOF
  申请人：AHAMMUNE BIOSCIENCES PRIVATE LIMITED

  公开号：US20200255417A1

  公开（公告）日：2020-08-13

  The present invention relates to novel thiophene compounds of general Formula I, and their stereoisomers tures, geometrical isomers, tautomers, pharmaceutically acceptable salts, hydrates, solvates, solid forms and mixtures thereof along with process for their preparation. The present invention discloses compounds that are useful in the treatment and prevention of autoimmune diseases.
• US4432992A
  申请人：——

  公开号：US4432992A

  公开（公告）日：1984-02-21
• Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents
  作者：Toshiya Noguchi、Masahiro Hasegawa、Kazuyuki Tomisawa、Morihiro Mitsukuchi

  DOI：10.1016/j.bmc.2003.08.009

  日期：2003.11

  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.