(E)-4-(2-((3,4,5-trimethoxyphenyl)sulfonyl)vinyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-(2-((3,4,5-trimethoxyphenyl)sulfonyl)vinyl)phenol
• 英文别名: 4-[(E)-2-(3,4,5-trimethoxyphenyl)sulfonylethenyl]phenol
• 化学式: C₁₇H₁₈O₆S
• 分子量: 350.392
• InChiKey: OHIZUVLVFLQMFM-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 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：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  O-ethyl S-(3,4,5-trimethoxyphenyl)carbonodithioate 在 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.75h， 生成 (E)-4-(2-((3,4,5-trimethoxyphenyl)sulfonyl)vinyl)phenol
  参考文献：
  名称：

  一种含砜类取代的查尔酮类似物、其制备方法及其医药用途

  摘要：

  本发明涉及药物化学领域，具体涉及一类新的砜类查尔酮类似物及其制备方法。本发明还公开了含有所属化合物的药用组合物和所述化合物在治疗肿瘤以及通过抑制微管蛋白活性来治疗其他疾病或病症中的应用。

  公开号：

  CN108191719A

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.