1-((1H-tetrazol-5-yl)methyl)pyrimidine-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((1H-tetrazol-5-yl)methyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-(2H-tetrazol-5-ylmethyl)pyrimidine-2,4-dione
• 化学式: C₆H₆N₆O₂
• 分子量: 194.153
• InChiKey: VUNFWIWECBVRFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-((1H-tetrazol-5-yl)methyl)pyrimidine-2,4(1H,3H)-dione 、 2-溴乙醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以18%的产率得到1-(((2-hydroxyethyl)-1,2,3,4-tetrazol-5-yl)methyl)pyrimidin-2,4-dione
  参考文献：
  名称：

  One-pot click synthesis of 1,2,3-triazole-embedded unsaturated uracil derivatives and hybrids of 1,5- and 2,5-disubstituted tetrazoles and pyrimidines

  摘要：

  Novel conformationally restricted pyrimidine derivatives with a 1,2,3-triazolyl scaffold bound via Z- and E-2-butenyl spacers were prepared by Cu(I)-catalyzed click chemistry via a one-pot, multi-step reaction under microwave irradiation, while 1,5- and 2,5-disubstituted tetrazoles were synthesized by convenient, environmentally friendly click synthesis and subsequently by N-alkylation of 5-substituted 1H-tetrazoles. Among all the tested compounds, the N-1,N-3-disubstituted olefinic uracil derivative showed the highest antiproliferative effects. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.152
• 作为产物：
  描述：

  1-(cyanomethyl)uracyl 在 sodium azide 、 维生素 C 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以80%的产率得到1-((1H-tetrazol-5-yl)methyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  某些四唑衍生物的合成，抗真菌评价和分子对接研究

  摘要：

  在铜双（二乙酰姜黄素）1,2-二氨基苯席夫碱铜配合物SiO 2-[Cu-描述了在抗坏血酸和水/ i-PrOH（50:50，V / V）介质在回流条件下存在下作为非均相催化剂的[BDACDABSBC]。通过将双（二乙酰姜黄素）铜1,2-二氨基苯希夫碱配合物[Cu-BDACDABSBC]固定在硅胶上制备负载型催化剂。该络合物具有高选择性，催化活性和可回收性。该过程的显着特征是高产量，广泛的基材范围以及简单而有效的后处理过程。根据这种综合方法，合成了具有生物活性N-杂环核心的5取代1 H-四唑的优异收率。筛选了标题化合物的体外抗真菌活性，以对抗各种致病性真菌菌株，例如涉及白色念珠菌，光滑念珠菌，克鲁氏梭菌，近生念珠菌的念珠菌以及由烟曲霉和烟曲霉组成的丝状真菌如曲霉。黄曲霉 讨论了一种最有效的抗真菌化合物的分子对接分析。对接研究确定了最有效的化合物与分枝杆菌P450DM的活性位点之间的显着相互作用

  DOI：

  10.17344/acsi.2019.4992

文献信息

• Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5-Substituted-1<i>H</i>-Tetrazole Derivatives Tethered to Bioactive<i>N</i>-Heterocyclic Cores
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Vahid Sadeghi Dehchenari、S. Jafar Hoseini

  DOI：10.1002/jhet.2591

  日期：2017.1

  bioactive N‐heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3 in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r‐GO nanohybrid) as a heterogeneous nanocatalyst in water/i‐PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount

  在存在铜/氨基粘土/还原氧化石墨烯纳米杂化物（铜）的情况下，通过烷基腈（RCN）和NaN 3之间的[3 + 2]环加成反应，合成了一系列具有生物活性N杂环核的5位取代的1 H-四唑。/ AC / R-GO纳米杂化物）作为在水中的纳米催化剂的异构/我‐PrOH（50:50，V / V）介质在回流条件下。讨论了因素对样品反应的影响，包括溶剂类型，温度和催化剂用量。该当前协议具有许多优点，包括价格便宜，对环境无害，基材范围广，产率高以及易于处理。该协议中使用的Cu / AC / r-GO是一种低成本催化剂，被证明具有相当大的化学和热稳定性。这种非吸湿性催化剂可以轻松回收，再利用和存储，以进行许多连续的反应，而不会显着降低反应活性。
• An Efficient Protocol for Facile Synthesis of New 5-Substituted-1<i>H</i>-Tetrazole Derivatives Using Copper-Doped Silica Cuprous Sulfate (CDSCS) as Heterogeneous Nano-Catalyst
  作者：Mohammad Navid Soltani Rad

  DOI：10.5935/0103-5053.20160138

  日期：——

  A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted1H-tetrazoles in good to excellent yields (up to 93%). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.