5-[(4-bromophenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1H-[1,2,4]triazole-3-carboxamide | 1106736-37-1

• 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
• 英文名称: 5-[(4-bromophenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1H-[1,2,4]triazole-3-carboxamide
• 英文别名: 5-[2-(4-Bromophenyl)ethynyl]-1-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide
• CAS: 1106736-37-1
• 化学式: C₁₄H₁₃BrN₄O₃
• 分子量: 365.186
• InChiKey: DQNSDIDAZQYTHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-[(4-bromophenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1H-[1,2,4]triazole-3-carboxamide 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以80%的产率得到
  参考文献：
  名称：

  A novel arylethynyltriazole acyclonucleoside inhibits proliferation of drug-resistant pancreatic cancer cells

  摘要：

  Novel arylethynyltriazole acyclonucleosides were synthesized and assessed for their anticancer activity on drug-resistant pancreatic cancer MiaPaCa-2 cells. One lead compound was found to have much more potent apoptosis-related antiproliferative effects than gemcitabine, the current first-line treatment for pancreatic cancer. Further investigations showed that this active compound did not inhibit DNA synthesis, which means that it does not resemble gemcitabine and may involve a different mechanism of action. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.093
• 作为产物：
  描述：

  5-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide 、 (4-溴苯基)乙炔 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48%的产率得到5-[(4-bromophenyl)ethynyl]-1-[(2-hydroxyethoxy)methyl]-1H-[1,2,4]triazole-3-carboxamide
  参考文献：
  名称：

  A novel arylethynyltriazole acyclonucleoside inhibits proliferation of drug-resistant pancreatic cancer cells

  摘要：

  Novel arylethynyltriazole acyclonucleosides were synthesized and assessed for their anticancer activity on drug-resistant pancreatic cancer MiaPaCa-2 cells. One lead compound was found to have much more potent apoptosis-related antiproliferative effects than gemcitabine, the current first-line treatment for pancreatic cancer. Further investigations showed that this active compound did not inhibit DNA synthesis, which means that it does not resemble gemcitabine and may involve a different mechanism of action. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.093

文献信息

• NOVEL TRIAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS
  申请人：Inserm Transfert

  公开号：EP2279193A1

  公开（公告）日：2011-02-02
• US8563526B2
  申请人：——

  公开号：US8563526B2

  公开（公告）日：2013-10-22
• [EN] NOVEL VIRAL REPLICATION INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE RÉPLICATION VIRALE
  申请人：UNIV LEUVEN KATH

  公开号：WO2009015446A2

  公开（公告）日：2009-02-05

  The present invention relates to novel compounds and to their use as a medicament, more in particular for the treatment or prevention of viral infections in mammals. The invention also relates to processes for the preparation of compounds according to the invention and to pharmaceutical compositions comprising them.
• [EN] NOVEL TRIAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS<br/>[FR] NOUVEAUX DÉRIVÉS DE TRIAZOLE, LEUR PRÉPARATION ET LEUR APPLICATION EN THÉRAPEUTIQUE
  申请人：INSERM TRANSFERT

  公开号：WO2009133147A1

  公开（公告）日：2009-11-05

  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.
• A novel arylethynyltriazole acyclonucleoside inhibits proliferation of drug-resistant pancreatic cancer cells
  作者：Menghua Wang、Yi Xia、Yuting Fan、Palma Rocchi、Fanqi Qu、Juan L. Iovanna、Ling Peng

  DOI：10.1016/j.bmcl.2010.08.093

  日期：2010.10

  Novel arylethynyltriazole acyclonucleosides were synthesized and assessed for their anticancer activity on drug-resistant pancreatic cancer MiaPaCa-2 cells. One lead compound was found to have much more potent apoptosis-related antiproliferative effects than gemcitabine, the current first-line treatment for pancreatic cancer. Further investigations showed that this active compound did not inhibit DNA synthesis, which means that it does not resemble gemcitabine and may involve a different mechanism of action. (c) 2010 Elsevier Ltd. All rights reserved.