(E)-2-methoxy-5-(2-((3,4,5-trimethoxyphenyl)sulfinyl)prop-1-en-1-yl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-methoxy-5-(2-((3,4,5-trimethoxyphenyl)sulfinyl)prop-1-en-1-yl)phenol
• 英文别名: 2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)sulfinylprop-1-enyl]phenol
• 化学式: C₁₉H₂₂O₆S
• 分子量: 378.446
• InChiKey: NCNPYWOENQNRPY-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  O-ethyl S-(3,4,5-trimethoxyphenyl)carbonodithioate 在 正丁基锂 、 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.42h， 生成 (E)-2-methoxy-5-(2-((3,4,5-trimethoxyphenyl)sulfinyl)prop-1-en-1-yl)phenol
  参考文献：
  名称：

  Discovery of novel vinyl sulfone derivatives as anti-tumor agents with microtubule polymerization inhibitory and vascular disrupting activities

  摘要：

  Vinyl sulfone or sulfoxide moieties were firstly introduced to the structure of chalcone compound by replacing the carbonyl group to afford a series of novel compounds as potential anti-tubulin agents. All of the target compounds were evaluated for their anti-proliferative activity. Among them, compound 12m showed the most potent activity against a panel of cancer cell lines with IC50 values ranging from 0.128 to 0.606 mu M. Further mechanism studies demonstrated that compound 12m caused G2/M phase arrest, induced cell apoptosis and disrupted the intracellular microtubule network. Moreover, compound 12m reduced the cell migration and disrupted the capillary-like tube formation in human umbilical vein endothelial cell (HUVEC) assays. Importantly, compound 12m significantly and dose dependently inhibited tumor growth in H22 liver cancer allograft mouse model, which is more potent than control compound CA-4, suggesting that 12m deserves further research as a potential anti-tubulin agent targeting colchicine binding site on tubulin. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.074

文献信息

• Discovery of novel vinyl sulfone derivatives as anti-tumor agents with microtubule polymerization inhibitory and vascular disrupting activities
  作者：Wenlong Li、Ying Yin、Hong Yao、Wen Shuai、Honghao Sun、Shengtao Xu、Jie Liu、Hequan Yao、Zheying Zhu、Jinyi Xu

  DOI：10.1016/j.ejmech.2018.08.074

  日期：2018.9

  Vinyl sulfone or sulfoxide moieties were firstly introduced to the structure of chalcone compound by replacing the carbonyl group to afford a series of novel compounds as potential anti-tubulin agents. All of the target compounds were evaluated for their anti-proliferative activity. Among them, compound 12m showed the most potent activity against a panel of cancer cell lines with IC50 values ranging from 0.128 to 0.606 mu M. Further mechanism studies demonstrated that compound 12m caused G2/M phase arrest, induced cell apoptosis and disrupted the intracellular microtubule network. Moreover, compound 12m reduced the cell migration and disrupted the capillary-like tube formation in human umbilical vein endothelial cell (HUVEC) assays. Importantly, compound 12m significantly and dose dependently inhibited tumor growth in H22 liver cancer allograft mouse model, which is more potent than control compound CA-4, suggesting that 12m deserves further research as a potential anti-tubulin agent targeting colchicine binding site on tubulin. (C) 2018 Elsevier Masson SAS. All rights reserved.