(E)-2-(4-methanesulfonylphenyl)-3-(3-bromo-4-hydroxyphenyl)acrylic acid | 891149-35-2

• 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-methanesulfonylphenyl)-3-(3-bromo-4-hydroxyphenyl)acrylic acid
• 英文别名: (E)-2-(4-methylsulfonylphenyl)-3-(3-bromo-4-hydroxyphenyl)acrylic acid；(E)-3-(3-bromo-4-hydroxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid
• CAS: 891149-35-2
• 化学式: C₁₆H₁₃BrO₅S
• 分子量: 397.246
• InChiKey: YTBXMNHYASPWTD-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  91.67
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-methanesulfonylphenyl)-3-(3-bromo-4-hydroxyphenyl)acrylic acid 在 硫酸 作用下， 反应 8.0h， 生成 ethyl (E)-3-(4-acetyloxy-3-bromophenyl)-2-(4-methylsulfonylphenyl)prop-2-enoate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives

  摘要：

  A series of 4-hydroxybenzene acrylic acid derivatives were designed and synthesized based on the ferulic acid of natural active ingredients. The tested compound 5a, 5f and 6a have significant anti-inflammatory activity with suppression rates of 45.29%, 44.75% and 24.11%, respectively, compared with that of indomethacin, and their cardiac toxicity was not observed. The structure-function relationship shows that the p-hydroxyl group on the a-position benzene ring, particularly if acetylated, contributes to the considerable anti-inflammatory activity; that the carboxyl group on the double bond, if esterified, also contributes to the anti-inflammatory activity; that the p-methylsulfonyl group on the other benzene ring, whose introduction is due to the COX-2 selectivity, also contributes to anti-inflammatory activity surprisingly. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.063
• 作为产物：
  描述：

  茴香硫醚 在 吗啉 、 aluminum (III) chloride 、 磷酸 、 双氧水 、 乙酸酐 、 sulfur 、 三乙胺 、 sodium hydroxide 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 28.5h， 生成 (E)-2-(4-methanesulfonylphenyl)-3-(3-bromo-4-hydroxyphenyl)acrylic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives

  摘要：

  A series of 4-hydroxybenzene acrylic acid derivatives were designed and synthesized based on the ferulic acid of natural active ingredients. The tested compound 5a, 5f and 6a have significant anti-inflammatory activity with suppression rates of 45.29%, 44.75% and 24.11%, respectively, compared with that of indomethacin, and their cardiac toxicity was not observed. The structure-function relationship shows that the p-hydroxyl group on the a-position benzene ring, particularly if acetylated, contributes to the considerable anti-inflammatory activity; that the carboxyl group on the double bond, if esterified, also contributes to the anti-inflammatory activity; that the p-methylsulfonyl group on the other benzene ring, whose introduction is due to the COX-2 selectivity, also contributes to anti-inflammatory activity surprisingly. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.063

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。
• Design, synthesis, antiviral activities of ferulic acid derivatives
  作者：Jin-long Mao、Lei Wang、Shu-jie Chen、Bin Yan、Li-ying Xun、Rui-cheng Li、Pei-chen Wang、Qi-tao Zhao

  DOI：10.3389/fphar.2023.1133655

  日期：——

  A series of novel ferulic acid derivatives were designed and synthesized, and the twenty-one compounds were evaluated for their antiviral activities against Respiratory syncytial virus (RSV), herpes simplex virus type 1 (HSV-1), and enterovirus type 71 (EV71). These derivatives with the core structure of diphenyl acrylic acids had cis-trans isomers, which were confirmed by 1H NMR, HPLC, and UV-vis

  设计并合成了一系列新型阿魏酸衍生物，并评价了 21 种化合物对呼吸道合胞病毒 (RSV)、单纯疱疹病毒 1 型 (HSV-1) 和肠道病毒 71 型 (EV71) 的抗病毒活性. 这些以二苯基丙烯酸为核心结构的衍生物具有顺反式同分异构体，经证实1个首次获得 H NMR、HPLC 和 UV-vis 光谱。A5 对 RSV 有选择性作用，但对 1 型单纯疱疹病毒和 71 型肠道病毒没有作用，其治疗指数 (TI) 为 32，明显优于阿魏酸。A5对自由基无清除作用，但A2作为A5的降解产物对DPPH·和ABTS有明显的清除作用+·. 此外，A5对内皮细胞无毒性，甚至显示出增殖作用。因此，A5作为先导化合物值得进一步优化其结构，研究抑制呼吸道合胞病毒的机制。