3-ethyl-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-ethyl-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene
• 英文别名: 3-[1-(3-Ethylphenyl)triazol-4-yl]propan-1-ol；3-[1-(3-ethylphenyl)triazol-4-yl]propan-1-ol
• 化学式: C₁₃H₁₇N₃O
• mdl: MFCD27019529
• 分子量: 231.297
• InChiKey: DAOSJYIMLALWFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethyl-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-ethyl-(4-(3-(tosyloxy)propyl)-1H-1,2,3-triazol-1-yl)benzene
  参考文献：
  名称：

  Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

  摘要：

  Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteasome. We previously published a study exploring the aryl sulfonate ester of cjoc42 in an effort to enhance gankyrin binding and inhibit cancer cell proliferation. In order to further improve the gankyrin binding ability of the cjoc42 scaffold, an extensive SAR for the aryl-triazole moiety of cjoc42 was developed. Our cjoc42 derivatives exhibited enhanced gankyrin binding, as well as enhanced antiproliferative activity against Hep3B, HepG2, A549, and MDA-MB-231 cancer cell lines.

  DOI：

  10.1016/j.bmcl.2020.127372
• 作为产物：
  描述：

  3-乙基苯胺 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 3-ethyl-(4-(3-hydroxypropyl)-1H-1,2,3-triazol-1-yl)benzene
  参考文献：
  名称：

  Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

  摘要：

  Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteasome. We previously published a study exploring the aryl sulfonate ester of cjoc42 in an effort to enhance gankyrin binding and inhibit cancer cell proliferation. In order to further improve the gankyrin binding ability of the cjoc42 scaffold, an extensive SAR for the aryl-triazole moiety of cjoc42 was developed. Our cjoc42 derivatives exhibited enhanced gankyrin binding, as well as enhanced antiproliferative activity against Hep3B, HepG2, A549, and MDA-MB-231 cancer cell lines.

  DOI：

  10.1016/j.bmcl.2020.127372