(E)-3-(4-methoxyphenyl)-N-(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)acrylamide | 1360538-33-5

• 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-methoxyphenyl)-N-(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)acrylamide
• 英文别名: (E)-3-(4-methoxyphenyl)-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]prop-2-enamide
• CAS: 1360538-33-5
• 化学式: C₁₉H₁₇N₃O₂S
• 分子量: 351.429
• InChiKey: LEFPCMMZXLVDQX-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲基苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (E)-3-(4-methoxyphenyl)-N-(5-(p-tolyl)-1,3,4-thiadiazol-2-yl)acrylamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amide derivatives as novel antitubulin agents

  摘要：

  A series of cinnamic acyl 1,3,4-thiadiazole amide derivatives (6a-10e) have been designed and synthesized, and their biological activities were also evaluated as potential antiproliferation and tubulin polymerization inhibitors. Among all the compounds, 10e showed the most potent activity in vitro, which inhibited the growth of MCF-7 and A549 cell lines with IC50 values of 0.28 and 0.52 mu g/mL, respectively. Compound 10e also exhibited significant tubulin polymerization inhibitory activity (IC50 = 1.16 mu g/mL). Docking simulation was performed to insert compound 10e into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 10e with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.057

文献信息

• Synthesis, biological evaluation, and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amide derivatives as novel antitubulin agents
  作者：Xian-Hui Yang、Qing Wen、Ting-Ting Zhao、Jian Sun、Xi Li、Man Xing、Xiang Lu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.12.057

  日期：2012.2

  A series of cinnamic acyl 1,3,4-thiadiazole amide derivatives (6a-10e) have been designed and synthesized, and their biological activities were also evaluated as potential antiproliferation and tubulin polymerization inhibitors. Among all the compounds, 10e showed the most potent activity in vitro, which inhibited the growth of MCF-7 and A549 cell lines with IC50 values of 0.28 and 0.52 mu g/mL, respectively. Compound 10e also exhibited significant tubulin polymerization inhibitory activity (IC50 = 1.16 mu g/mL). Docking simulation was performed to insert compound 10e into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 10e with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.