5-[(1-环己烯)乙炔基]-1-[(2-羟基乙氧基)甲基]-1,2,4-三唑-3-甲酰胺 | 1041860-79-0

• 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-环己烯)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-cyclohexene)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide
• 英文别名: 5-[2-(Cyclohexen-1-yl)ethynyl]-1-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide
• CAS: 1041860-79-0
• 化学式: C₁₄H₁₈N₄O₃
• 分子量: 290.322
• InChiKey: WLZXXKDRTYVCDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(1-环己烯)乙炔基]-1-[(2-羟基乙氧基)甲基]-1,2,4-三唑-3-甲酰胺 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以40%的产率得到5-[5-(cyclohexen-1-yl)-2H-triazol-4-yl]-1-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Bitriazolyl acyclonucleosides synthesized via Huisgen reaction using internal alkynes show antiviral activity against tobacco mosaic virus

  摘要：

  A family of novel bitriazolyl acyclonucleosides were synthesized using a simple and convenient one-step synthetic procedure via the Huisgen reaction by addition of NaN3 onto triazole nucleosides bearing internal alkynyl groups introduced at the 5-position of the triazole ring. Some of the compounds exhibited interesting antiviral activity against tobacco mosaic virus, demonstrating the importance of the bitriazolyl motif for the observed antiviral activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.141
• 作为产物：
  描述：

  5-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide 、 1-乙炔基环己烷 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90%的产率得到5-[(1-环己烯)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.
• Bitriazolyl acyclonucleosides synthesized via Huisgen reaction using internal alkynes show antiviral activity against tobacco mosaic virus
  作者：Menghua Wang、Ruizhi Zhu、Zhijin Fan、Yifeng Fu、Liang Feng、Jianhua Yao、Alain Maggiani、Yi Xia、Fanqi Qu、Ling Peng

  DOI：10.1016/j.bmcl.2010.10.141

  日期：2011.1

  A family of novel bitriazolyl acyclonucleosides were synthesized using a simple and convenient one-step synthetic procedure via the Huisgen reaction by addition of NaN3 onto triazole nucleosides bearing internal alkynyl groups introduced at the 5-position of the triazole ring. Some of the compounds exhibited interesting antiviral activity against tobacco mosaic virus, demonstrating the importance of the bitriazolyl motif for the observed antiviral activity. (C) 2010 Elsevier Ltd. All rights reserved.