5-[(1-环戊醇)乙炔基]-1-[(2-羟基乙氧基)甲基]-1,2,4-三唑-3-甲酰胺 | 1041860-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 5-[(1-环戊醇)乙炔基]-1-[(2-羟基乙氧基)甲基]-1,2,4-三唑-3-甲酰胺
• 英文名称: 5-[(1-cyclopentanol)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide
• 英文别名: 5-[2-(1-Hydroxycyclopentyl)ethynyl]-1-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide
• CAS: 1041860-76-7
• 化学式: C₁₃H₁₈N₄O₄
• 分子量: 294.31
• InChiKey: ZHQXKORLSFBETD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide 、 1-乙炔基环戊醇 在 copper(l) iodide 、 四(三苯基膦)钯 、 lithium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.42h， 以97%的产率得到5-[(1-环戊醇)乙炔基]-1-[(2-羟基乙氧基)甲基]-1,2,4-三唑-3-甲酰胺
  参考文献：
  名称：

  Arylethynyltriazole acyclonucleosides inhibit hepatitis C virus replication

  摘要：

  Novel acyclic triazole nucleosides with various ethynyl moieties appended on the triazole nucleobase were synthesized efficiently using a convenient one-step Sonogashira reaction in aqueous solution and under microwave irradiation. One of the compounds, 1f, inhibited HCV subgenomic replication with a 50% effective concentration (EC50) of 22 mu g/ml and did not inhibit proliferation of the host cell at a concentration of 50 mu g/ml. A preliminary SAR study suggests that the appended phenyl ring as well as the rigid triple bond linker contributes importantly to the anti-HCV activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.026

文献信息

• Arylethynyltriazole acyclonucleosides inhibit hepatitis C virus replication
  作者：Ruizhi Zhu、Menghua Wang、Yi Xia、Fanqi Qu、Johan Neyts、Ling Peng

  DOI：10.1016/j.bmcl.2008.04.026

  日期：2008.6

  Novel acyclic triazole nucleosides with various ethynyl moieties appended on the triazole nucleobase were synthesized efficiently using a convenient one-step Sonogashira reaction in aqueous solution and under microwave irradiation. One of the compounds, 1f, inhibited HCV subgenomic replication with a 50% effective concentration (EC50) of 22 mu g/ml and did not inhibit proliferation of the host cell at a concentration of 50 mu g/ml. A preliminary SAR study suggests that the appended phenyl ring as well as the rigid triple bond linker contributes importantly to the anti-HCV activity. (C) 2008 Elsevier Ltd. All rights reserved.