5-[(4-trifluoromethylphenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide | 1041860-72-3

• 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: 5-[(4-trifluoromethylphenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide
• 英文别名: 1-(2-Hydroxyethoxymethyl)-5-[2-[4-(trifluoromethyl)phenyl]ethynyl]-1,2,4-triazole-3-carboxamide
• CAS: 1041860-72-3
• 化学式: C₁₅H₁₃F₃N₄O₃
• 分子量: 354.288
• InChiKey: DGVXEJLSUHTSEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[(4-trifluoromethylphenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以53%的产率得到1-(2-hydroxyethoxymethyl)-5-[5-[4-(trifluoromethyl)phenyl]-2H-triazol-4-yl]-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 、 4-乙炔基-α,α,α-三氟甲苯 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75%的产率得到5-[(4-trifluoromethylphenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide
  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

• Discovery of Novel Arylethynyltriazole Ribonucleosides with Selective and Effective Antiviral and Antiproliferative Activity
  作者：Jinqiao Wan、Yi Xia、Yang Liu、Menghua Wang、Palma Rocchi、Jianhua Yao、Fanqi Qu、Johan Neyts、Juan L. Iovanna、Ling Peng

  DOI：10.1021/jm800927r

  日期：2009.2.26

  Novel ethynyltriazole ribonucleosides were synthesized using a simple and efficient two-step procedure involving Sonogashira coupling and subsequent ammonolysis. Compounds 2f and 3o inhibited hepatitis C virus (HCV) replication efficiently, whereas compound 3f demonstrated potent apoptosis-induced antiproliferative activity against pancreatic cancer MiaPaCa-2 cells both in vitro and in vivo. Most interestingly, the notable selective antiviral and antiproliferative activities were achieved respectively for 2f and 3f by modulating the ribose sugar moiety into deprotected and protected forms while retaining a similar trifluoromethylphenylethynyltriazole as the nucleobase. Preliminary structure-activity relationship study revealed that not only the ribose moiety but also the CF3 group at the p-position of the phenyl ring and the rigid triple bond functionality contributed critically to the observed antiviral activity of 2f against HCV and antiproliferative activity of 3f against pancreatic cancer. These two compounds constitute therefore promising leads in the search for new antiviral and anticancer candidates.
• NOVEL TRIAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS
  申请人：Peng Ling

  公开号：US20110136754A1

  公开（公告）日：2011-06-09

  The present invention relates to novel compounds of formula (A): in the form of a free base or of an addition salt with an acid. The invention also relates to process of preparation of compounds of formula (A), to composition comprising them and to their application in therapeutics and in particular in cancers.
• US8563526B2
  申请人：——

  公开号：US8563526B2

  公开（公告）日：2013-10-22
• 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.