2-[4-(3,5-dimethylbenzyl)-5-ethyl-1,2,3-triazol-2-yl]ethanol

• 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: 2-[4-(3,5-dimethylbenzyl)-5-ethyl-1,2,3-triazol-2-yl]ethanol
• 英文别名: 2-[4-[(3,5-Dimethylphenyl)methyl]-5-ethyl-triazol-2-yl]ethanol；2-[4-[(3,5-dimethylphenyl)methyl]-5-ethyltriazol-2-yl]ethanol
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: VHKMETHJAFQRAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二甲基苯甲酸 在 三乙基硅烷 、 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 、 sodium azide 、 potassium carbonate 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.25h， 生成 2-[4-(3,5-dimethylbenzyl)-5-ethyl-1,2,3-triazol-2-yl]ethanol
  参考文献：
  名称：

  Application of the Huisgen cycloaddition and ‘click’ reaction toward various 1,2,3-triazoles as HIV non-nucleoside reverse transcriptase inhibitors

  摘要：

  The development of novel anti-HIV agents remains an important medicinal chemistry challenge given that no cure for the disease is imminent, and the continued use of current NNRTIs inevitably leads to problems associated with resistance. Inspired by the pyrazole-containing NNRTI lersivirine (LSV), we embarked upon a study to establish whether 1,2,3-triazole heterocycles could be used as a new scaffold for the creation of novel NNRTIs. An especially attractive feature of triazoles used for this purpose is the versatility in accessing variously functionalised systems using either the thermally regulated Huisgen cycloaddition, or the related 'click' reaction. Employing three alternative forms of these reactions, we were able to synthesise a range of triazole compounds and evaluate their efficacy in a phenotypic HIV assay. To our astonishment, even compounds closely mimicking LSV were only moderately effective against HIV. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.05.082

文献信息

• Application of the Huisgen cycloaddition and ‘click’ reaction toward various 1,2,3-triazoles as HIV non-nucleoside reverse transcriptase inhibitors
  作者：Nicole Pribut、Clinton G.L. Veale、Adriaan E. Basson、Willem A.L. van Otterlo、Stephen C. Pelly

  DOI：10.1016/j.bmcl.2016.05.082

  日期：2016.8

  The development of novel anti-HIV agents remains an important medicinal chemistry challenge given that no cure for the disease is imminent, and the continued use of current NNRTIs inevitably leads to problems associated with resistance. Inspired by the pyrazole-containing NNRTI lersivirine (LSV), we embarked upon a study to establish whether 1,2,3-triazole heterocycles could be used as a new scaffold for the creation of novel NNRTIs. An especially attractive feature of triazoles used for this purpose is the versatility in accessing variously functionalised systems using either the thermally regulated Huisgen cycloaddition, or the related 'click' reaction. Employing three alternative forms of these reactions, we were able to synthesise a range of triazole compounds and evaluate their efficacy in a phenotypic HIV assay. To our astonishment, even compounds closely mimicking LSV were only moderately effective against HIV. (C) 2016 Elsevier Ltd. All rights reserved.