(E)-3-(4-hydroxy-3-methoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid | 891149-12-5

• 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)-3-(4-hydroxy-3-methoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid
• CAS: 891149-12-5
• 化学式: C₁₇H₁₆O₆S
• 分子量: 348.376
• InChiKey: ZJZIUVHNFBMOLK-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-hydroxy-3-methoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid 在 硫酸 作用下， 反应 9.0h， 生成 ethyl (E)-3-(4-acetyloxy-3-methoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoate
  参考文献：
  名称：

  阿魏酸衍生物的设计、合成及抗病毒活性

  摘要：

  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。

  DOI：

  10.3389/fphar.2023.1133655
• 作为产物：
  描述：

  4-甲烷磺酰基苯乙酸 在 乙酸酐 、 三乙胺 、 sodium hydroxide 作用下， 反应 3.5h， 生成 (E)-3-(4-hydroxy-3-methoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic 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

• Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives
  作者：Jin-Long Mao、Xiang-Kai Ran、Jing-Zhen Tian、Bo Jiao、Hong-Lei Zhou、Li Chen、Zhen-Guo Wang

  DOI：10.1016/j.bmcl.2010.12.063

  日期：2011.3

  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.
• 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。