(E)-3-(4-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)acrylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)acrylic acid
• 英文别名: (E)-3-[4-[[1-(4-chlorophenyl)triazol-4-yl]methoxy]-3-methoxyphenyl]prop-2-enoic acid
• 化学式: C₁₉H₁₆ClN₃O₄
• 分子量: 385.807
• InChiKey: JVJONXIEDSSKMI-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.47
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  阿魏酸 在 copper(ll) sulfate pentahydrate 、 硫酸 、 potassium carbonate 、 sodium ascorbate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.25h， 生成 (E)-3-(4-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)acrylic acid
  参考文献：
  名称：

  Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX

  摘要：

  Carbonic anhydrase IX (CAIX) is an emerging drug target for hypoxia associated cancers. To identify potent and selective inhibitors of CAIX, a small library of ferulic acid (FA) derivatives bearing triazole moiety has been designed, synthesized and evaluated against different human CA isoforms (CAII, CAVA & CAIX). Though most of the compounds showed CAIX inhibition in the micromolar range, compound 7i selectively inhibits CAIX in the nanomolar range (IC₅₀ = 24 nM). In silico analysis revealed binding of 7i with the catalytically important amino acid residues of CAIX. Further, cell-based studies indicate that 7i inhibits the activity of CAIX, decreases the epithelial to mesenchymal transitions, induces apoptosis, inhibits cell migration and colonization potential of cancer cells. Taken together, these results emphasized the use of 7i as a prospective pharmacological lead molecule in CAIX targeted anticancer therapeutics.

  DOI：

  10.1016/j.bmc.2020.115424

文献信息

• Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX
  作者：Babita Aneja、Aarfa Queen、Parvez Khan、Farheen Shamsi、Afzal Hussain、Phool Hasan、M. Moshahid A. Rizvi、Constantin G. Daniliuc、Mohamed F. Alajmi、Mohd. Mohsin、Md. Imtaiyaz Hassan、Mohammad Abid

  DOI：10.1016/j.bmc.2020.115424

  日期：2020.5

  Carbonic anhydrase IX (CAIX) is an emerging drug target for hypoxia associated cancers. To identify potent and selective inhibitors of CAIX, a small library of ferulic acid (FA) derivatives bearing triazole moiety has been designed, synthesized and evaluated against different human CA isoforms (CAII, CAVA & CAIX). Though most of the compounds showed CAIX inhibition in the micromolar range, compound 7i selectively inhibits CAIX in the nanomolar range (IC₅₀ = 24 nM). In silico analysis revealed binding of 7i with the catalytically important amino acid residues of CAIX. Further, cell-based studies indicate that 7i inhibits the activity of CAIX, decreases the epithelial to mesenchymal transitions, induces apoptosis, inhibits cell migration and colonization potential of cancer cells. Taken together, these results emphasized the use of 7i as a prospective pharmacological lead molecule in CAIX targeted anticancer therapeutics.