3-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-5-carboxamide

• 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: 3-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-5-carboxamide
• 英文别名: 5-Bromo-2-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide；5-bromo-2-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide
• 化学式: C₆H₉BrN₄O₃
• 分子量: 265.066
• InChiKey: FPYFHUOVNMNOJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• 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：

  3-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-5-carboxamide 、 4-丙基苯乙炔 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 1.0h， 以88%的产率得到3-[2-p-propylphenylethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-5-carboxamide
  参考文献：
  名称：

  带有共平面芳基乙炔基三唑核碱基的无环核苷：合成，结构分析和生物学评估†

  摘要：

  在寻找生物活性化合物中，核苷衍生物是一类重要的分子。在我们不断努力开发新的核苷类似物的过程中，我们使用了Sonogashira交叉偶联反应来合成在三唑核碱基上带有各种芳基乙炔基的1,2,4-三唑无环核苷。通过使用3-碘三唑核苷作为偶联底物，Sonogashira反应即使在炔烃中也有效地进行，炔烃是众所周知的无反应性和挑战性的试剂。进一步的晶体结构分析揭示了3-芳基乙炔基三唑基序的共面特征，表明它们作为大型平面芳族系统或核碱基的替代物的潜力。最重要的是，几种合成的化合物对各种癌细胞均表现出令人感兴趣的抗增殖活性，并诱导了细胞凋亡，

  DOI：

  10.1039/c7nj01406f
• 作为产物：
  描述：

  methyl 3-bromo-1-[(2-acetoxyethoxy)methyl]-1,2,4-triazole-5-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以88%的产率得到3-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-5-carboxamide
  参考文献：
  名称：

  Direct synthesis of 5-aryltriazole acyclonucleosides via Suzuki coupling in aqueous solution

  摘要：

  5-Aryltriazole acyclonucleosides with various aromatic groups on the triazole ring were synthesized via the Suzuki coupling reaction in aqueous solution and promoted by microwave irradiation. Careful optimization of the reaction conditions led in good to excellent yields to the Suzuki products, while the cyclization side-reaction could be completely suppressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.154

文献信息

• Novel Triazole Ribonucleoside Down-Regulates Heat Shock Protein 27 and Induces Potent Anticancer Activity on Drug-Resistant Pancreatic Cancer
  作者：Yi Xia、Yang Liu、Jinqiao Wan、Menghua Wang、Palma Rocchi、Fanqi Qu、Juan L. Iovanna、Ling Peng

  DOI：10.1021/jm900960v

  日期：2009.10.8

  A series of novel 3-arylethynyltriazolyl ribonucleosides were synthesized and assessed for their anticancer activity on the drug-resistant pancreatic cancer cell line MiaPaCa-2. Among them, one compound exhibited potent apoptosis-inducing properties and anticancer activity against the pancreatic cancer model MiaPaCa-2 both in vitro and in vivo with no adverse effects. This compound did not inhibit DNA synthesis and therefore does not resemble the clinical drug gemcitabine. It did, however, significantly down-regulate the expression of heat shock protein 27 (Hsp27), a small molecular chaperone playing an important role in drug resistance and highly expressed in drug-resistant cancer forms, and thus represents the first small molecular anticancer lead with such a mode of action.
• Direct synthesis of 5-aryltriazole acyclonucleosides via Suzuki coupling in aqueous solution
  作者：Ruizhi Zhu、Fanqi Qu、Gilles Quéléver、Ling Peng

  DOI：10.1016/j.tetlet.2007.01.154

  日期：2007.3

  5-Aryltriazole acyclonucleosides with various aromatic groups on the triazole ring were synthesized via the Suzuki coupling reaction in aqueous solution and promoted by microwave irradiation. Careful optimization of the reaction conditions led in good to excellent yields to the Suzuki products, while the cyclization side-reaction could be completely suppressed. (c) 2007 Elsevier Ltd. All rights reserved.
• Acyclonucleosides bearing coplanar arylethynyltriazole nucleobases: synthesis, structural analysis, and biological evaluation
  作者：Mimi Chen、Zhengwei Zhou、Yaxiong Suo、Mengyao Li、Jianhua Yao、Ling Peng、Yi Xia

  DOI：10.1039/c7nj01406f

  日期：——

  of molecules in the search for bioactive compounds. In our continuing efforts to develop novel nucleoside analogs, we used the Sonogashira cross-coupling reaction to synthesize 1,2,4-triazole acyclonucleosides bearing various arylethynyl groups on the triazole nucleobase. By employing 3-iodotriazole nucleoside as the coupling substrate, the Sonogashira reaction proceeded efficiently even with alkynes

  在寻找生物活性化合物中，核苷衍生物是一类重要的分子。在我们不断努力开发新的核苷类似物的过程中，我们使用了Sonogashira交叉偶联反应来合成在三唑核碱基上带有各种芳基乙炔基的1,2,4-三唑无环核苷。通过使用3-碘三唑核苷作为偶联底物，Sonogashira反应即使在炔烃中也有效地进行，炔烃是众所周知的无反应性和挑战性的试剂。进一步的晶体结构分析揭示了3-芳基乙炔基三唑基序的共面特征，表明它们作为大型平面芳族系统或核碱基的替代物的潜力。最重要的是，几种合成的化合物对各种癌细胞均表现出令人感兴趣的抗增殖活性，并诱导了细胞凋亡，