(E)-3-(3,4-dimethoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid | 891148-32-6

• 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-(3,4-dimethoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid
• CAS: 891148-32-6
• 化学式: C₁₈H₁₈O₆S
• 分子量: 362.403
• InChiKey: HYEGWFWKMIESPG-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)-2-(4-methylsulfonylphenyl)prop-2-enoic acid 在 sodium hydroxide 作用下， 反应 0.5h， 生成
  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：

  4-甲硫基苯乙酮 在 吗啉 、 磷酸 、 双氧水 、 乙酸酐 、 sulfur 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 生成 (E)-3-(3,4-dimethoxyphenyl)-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.