(E)-2-(3,4-dihydroxyphenyl)ethenesulfonic acid N-methyl-N-(phenethyl)amide | 1449784-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(3,4-dihydroxyphenyl)ethenesulfonic acid N-methyl-N-(phenethyl)amide
• 英文别名: (E)-2-(3,4-dihydroxyphenyl)-N-methyl-N-(2-phenylethyl)ethenesulfonamide
• CAS: 1449784-13-7
• 化学式: C₁₇H₁₉NO₄S
• 分子量: 333.408
• InChiKey: SWKRFPNPRZJQAP-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,4-dihydroxyphenyl)ethenesulfonic acid N-methyl-N-(phenethyl)amide 、 乙酸酐 在 吡啶 作用下， 以95%的产率得到(E)-2-(3,4-diacetoxyphenyl)ethenesulfonic acid N-methyl-N-(phenethyl)amide
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of (E)-3,4-dihydroxy styryl sulfonamides derivatives as multifunctional neuroprotective agents against oxidative and inflammatory injury

  摘要：

  A novel class of (E)-3,4-dihydroxy styryl sulfonamides and their 3,4-diacetylated derivatives as caffeic acid phenethyl ester (CAPE) analogs was designed and prepared for improving stability and solubility of the lead compound. Their neuroprotective properties were assessed by several models. The results showed that target compounds displayed positive free radical quenching abilities, superior to that of CAPE. Compounds 6j-k and 7j-k demonstrated remarkable protection effects against damage induced by hydrogen peroxide which were apparently stronger than that of CAPE. Most of target compounds could inhibit nitric oxide production. Additionally, target compounds showed high blood-brain barrier permeability. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.05.043
• 作为产物：
  描述：

  2-[methyl(phenethyl)sulfamoyl]acetic acid methyl ester 在 四氢吡咯 、 水 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (E)-2-(3,4-dihydroxyphenyl)ethenesulfonic acid N-methyl-N-(phenethyl)amide
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of (E)-3,4-dihydroxy styryl sulfonamides derivatives as multifunctional neuroprotective agents against oxidative and inflammatory injury

  摘要：

  A novel class of (E)-3,4-dihydroxy styryl sulfonamides and their 3,4-diacetylated derivatives as caffeic acid phenethyl ester (CAPE) analogs was designed and prepared for improving stability and solubility of the lead compound. Their neuroprotective properties were assessed by several models. The results showed that target compounds displayed positive free radical quenching abilities, superior to that of CAPE. Compounds 6j-k and 7j-k demonstrated remarkable protection effects against damage induced by hydrogen peroxide which were apparently stronger than that of CAPE. Most of target compounds could inhibit nitric oxide production. Additionally, target compounds showed high blood-brain barrier permeability. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.05.043

文献信息

• Design, synthesis and pharmacological evaluation of (E)-3,4-dihydroxy styryl sulfonamides derivatives as multifunctional neuroprotective agents against oxidative and inflammatory injury
  作者：Xianling Ning、Ying Guo、Xiaoyan Ma、Renzong Zhu、Chao Tian、Zhili Zhang、Xiaowei Wang、Zhizhong Ma、Junyi Liu

  DOI：10.1016/j.bmc.2013.05.043

  日期：2013.9

  A novel class of (E)-3,4-dihydroxy styryl sulfonamides and their 3,4-diacetylated derivatives as caffeic acid phenethyl ester (CAPE) analogs was designed and prepared for improving stability and solubility of the lead compound. Their neuroprotective properties were assessed by several models. The results showed that target compounds displayed positive free radical quenching abilities, superior to that of CAPE. Compounds 6j-k and 7j-k demonstrated remarkable protection effects against damage induced by hydrogen peroxide which were apparently stronger than that of CAPE. Most of target compounds could inhibit nitric oxide production. Additionally, target compounds showed high blood-brain barrier permeability. (C) 2013 Published by Elsevier Ltd.