2-(4-chlorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole | 1344999-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(4-chlorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole
• 英文别名: 2-[(4-Chlorophenyl)methylsulfanyl]-5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3,4-oxadiazole
• CAS: 1344999-33-2
• 化学式: C₁₇H₁₃ClN₂O₃S
• 分子量: 360.821
• InChiKey: PYAJAGYSRQPQQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氢-1,4-苯并二噁烷-6-羧酸 在 硫酸 、 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(4-chlorobenzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents

  摘要：

  In present study, a series of new 1,3,4-oxadiazole derivatives containing 1,4-benzodioxan moiety (6a-6s) as potential telomerase inhibitors were synthesized. The bioassay tests demonstrated that compounds 6k, 6l, 6m, 6n and 6s exhibited broad-spectrum antitumor activity with IC50 concentration range from 7.21 mu M to 25.87 mu M against the four cancer cell lines, HEPG2, HELA, SW1116 and BGC823. Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. The results showed compound 6k possessed the most potent telomerase activity (IC50 = 1.27 +/- 0.05 mu M). Docking simulation was performed to position compound 6k into the active site of telomerase (3DU6) to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.013

文献信息

• Synthesis, biological evaluation, and molecular docking studies of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents
  作者：Xiao-Min Zhang、Min Qiu、Juan Sun、Yan-Bin Zhang、Yu-Shun Yang、Xiao-Liang Wang、Jian-Feng Tang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2011.08.013

  日期：2011.11

  In present study, a series of new 1,3,4-oxadiazole derivatives containing 1,4-benzodioxan moiety (6a-6s) as potential telomerase inhibitors were synthesized. The bioassay tests demonstrated that compounds 6k, 6l, 6m, 6n and 6s exhibited broad-spectrum antitumor activity with IC50 concentration range from 7.21 mu M to 25.87 mu M against the four cancer cell lines, HEPG2, HELA, SW1116 and BGC823. Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. The results showed compound 6k possessed the most potent telomerase activity (IC50 = 1.27 +/- 0.05 mu M). Docking simulation was performed to position compound 6k into the active site of telomerase (3DU6) to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.