(E)-2-(4-methylsulfonylphenyl)-3-phenylprop-2-enoic acid | 1283560-18-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(4-methylsulfonylphenyl)-3-phenylprop-2-enoic acid
• CAS: 1283560-18-8
• 化学式: C₁₆H₁₄O₄S
• 分子量: 302.351
• InChiKey: NEMYGZVTKXQVPT-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲烷磺酰基苯乙酸 、 苯甲醛 在 potassium acetate 、 乙酸酐 作用下， 反应 24.0h， 以49%的产率得到(E)-2-(4-methylsulfonylphenyl)-3-phenylprop-2-enoic acid
  参考文献：
  名称：

  2,3-Diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17β-hydroxysteroid dehydrogenase (AKR1C3)

  摘要：

  The aldo-keto reductase AKR1C3 is an important target for the development of new drugs. Selective inhibitors of this enzyme are needed because they should not inhibit other, structurally closely related AKR1C isoforms. A comprehensive series of 2,3-diarylpropenoic acids was synthesized and evaluated for the inhibition of AKR1C1-AKR1C3. We found that the 4-methylsulfonylphenyl substituent at position 2 of these acids is required to exhibit the selective inhibition of AKR1C3. The best results were obtained for the compounds that fulfill the above requirement and possess a 4-bromophenyl, 4-methylthiophenyl, 4-methylphenyl or 4-ethylphenyl substituent at position 3 of the substituted propenoic acids (i.e., acids 28, 29, 37, and 39, respectively). These compounds represent an important step toward the development of drug candidates for a treatment of the hormone-dependent and hormone-independent forms of prostate and breast cancers. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.045

文献信息

• Synthesis, configurational analysis and antiviral activities of novel diphenylacrylic acids with caffeic acid as the lead compound
  作者：Hui Zhou、Shi-jie Gao、Meng-tian Zhang、Jia Jia、Fei-xiang Chen、Cheng-long Chen、Peng-Fei Yang、Jin-long Mao

  DOI：10.1016/j.molstruc.2023.136016

  日期：2023.11

  series of novel caffeic acid derivatives with the core structure of diphenylacrylic acids were designed and synthesized. The 24 compounds involved were confirmed by NMR spectra (1H NMR, 13C NMR, HMQC or HMBC) and evaluated for their antiviral activities against RSV, HSV-1 and EV71. These derivatives exist as (E)- or (Z)- isomers of diphenylacrylic acid, and the configurational analysis method was illustrated

  设计合成了一系列以二苯基丙烯酸为核心结构的新型咖啡酸衍生物。所涉及的24种化合物均通过NMR谱（1 H NMR、13 C NMR、HMQC或HMBC）进行了确认，并评估了它们对RSV、HSV-1和EV71的抗病毒活性。这些衍生物以二苯基丙烯酸的( E )-或( Z )-异构体存在，并且首次通过1 H NMR阐明了构型分析方法。潜在的A2对HSV-1表现出选择性作用，但对RSV和EV71作用较弱，治疗指数（TI）为32，明显优于利巴韦林和咖啡酸。此外，A2对DPPH•和ABTS•有明显的清除作用。+并对肝细胞L02细胞的氧化损伤显示出保护作用。此外，分子对接研究表明，与咖啡酸相比，A2 对 HSV-1 靶点具有更好的结合亲和力。因此，A2值得作为先导化合物进一步筛选并研究其抑制HSV-1的机制。