5-溴-4-(呋喃-2-基)嘧啶 | 1489552-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴-4-(呋喃-2-基)嘧啶
• 英文名称: 5-bromo-4-(furan-2-yl)pyrimidine
• 英文别名: 5-Bromo-4-(furan-2-yl)pyrimidine
• CAS: 1489552-30-8
• 化学式: C₈H₅BrN₂O
• 分子量: 225.044
• InChiKey: CJPOSITZOPXTCP-UHFFFAOYSA-N

物化性质

• 沸点：
  302.4±27.0 °C(Predicted)
• 密度：
  1.605±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-溴-4-(呋喃-2-基)嘧啶 在 硫酸 、 硝酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以56%的产率得到5-bromo-4-(5-nitrofuran-2-yl)pyrimidine
  参考文献：
  名称：

  新型5-芳基-4-（5-硝基呋喃-2-基）-嘧啶类化合物的合成及生物学评价

  摘要：

  已经开发了一种容易的两步合成方法，用于从容易获得的5-溴-4-（呋喃-2-基）嘧啶中氟化和非氟化的5-芳基-4-（5-硝基呋喃-2-基）-嘧啶。体外筛选所有合成的化合物对十二种不同细菌菌株的抗菌活性。已证明这些化合物中的一些对淋病奈瑟氏球菌和金黄色葡萄球菌菌株显示出显着的抗菌活性，与市售的壮观霉素相当甚至更高。

  DOI：

  10.1016/j.bmcl.2017.05.013
• 作为产物：
  描述：

  呋喃 、 5-溴嘧啶 以 三氟乙酸 为溶剂， 反应 24.0h， 以64%的产率得到5-溴-4-(呋喃-2-基)嘧啶
  参考文献：
  名称：

  Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions

  摘要：

  Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv, avium, terrae, and multidrug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.006

文献信息

• Synthesis and evaluation of antitubercular activity of fluorinated 5-aryl-4-(hetero)aryl substituted pyrimidines
  作者：Egor V. Verbitskiy、Svetlana A. Baskakova、Marionella A. Kravchenko、Sergey N. Skornyakov、Gennady L. Rusinov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.bmc.2016.06.020

  日期：2016.8

  substitution of hydrogen (SNH) reactions starting from commercially available 5-bromopyrimidine and their antitubercular activity against Mycobacterium tuberculosis H37Rv has been explored. The outcome of the study disclose that, some of the compounds have showed promising activity in micromolar concentration against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant

  各种5-（氟化芳基）-4-（杂）芳基取代的嘧啶已经基于氢气的Suzuki交叉偶联和亲核芳香取代被合成（S Ñ ħ）反应从市售的5-溴嘧啶开始和其对抗结核活性分枝杆菌已经研究了结核H 37 Rv。研究结果表明，某些化合物以微摩尔浓度显示出对结核分枝杆菌H 37 Rv，鸟分枝杆菌，土地分枝杆菌有希望的活性。，以及从乌拉尔地区（俄罗斯）的结核病患者中分离出的多药耐药菌株。已经讨论了有关氟化化合物“结构-活性”关系的数据。
• New 5-arylamino-4-(5-nitrofuran-2-yl)pyrimidines as promising antibacterial agents
  作者：Egor V. Verbitskiy、Svetlana A. Baskakova、Natal’ya A. Gerasimova、Natal’ya P. Evstigneeva、Natal’ya V. Zil’berberg、Nikolay V. Kungurov、Marionella A. Kravchenko、Gennady L. Rusinov、Oleg N. Chupakhina、Valery N. Charushin

  DOI：10.1016/j.mencom.2018.07.017

  日期：2018.7

  A facile synthetic approach to 5-arylamino-4-(5-nitrofuran-2-yl)pyrimidines by the Buchwald-Hartwig cross-coupling with various anilines has been developed. All synthesized compounds demonstrated a significant level of in vitro antibacterial activity against Neisseria gonorrhoeae, Streptococcus pyogenes and Staphylococcus aureus, including their drug-resistant strains, which is much higher than that of the commercial drug Spectinomycin.
• Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions
  作者：Marionella A. Kravchenko、Egor V. Verbitskiy、Igor D. Medvinskiy、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1016/j.bmcl.2014.05.006

  日期：2014.7

  Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv, avium, terrae, and multidrug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of novel 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines as potential anti-bacterial agents
  作者：Egor V. Verbitskiy、Svetlana A. Baskakova、Natal'ya A. Gerasimova、Natal'ya P. Evstigneeva、Natal'ya V. Zil'berberg、Nikolay V. Kungurov、Marionella A. Kravchenko、Sergey N. Skornyakov、Marina G. Pervova、Gennady L. Rusinov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.bmcl.2017.05.013

  日期：2017.7

  synthetic approach to fluorinated and non-fluorinated 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines from readily available 5-bromo-4-(furan-2-yl)pyrimidine has been developed. All synthesized compounds were screened in vitro for their antibacterial activities against twelve various bacterial strains. It is demonstrated that some of these compounds exhibited significant antibacterial activities against strains

  已经开发了一种容易的两步合成方法，用于从容易获得的5-溴-4-（呋喃-2-基）嘧啶中氟化和非氟化的5-芳基-4-（5-硝基呋喃-2-基）-嘧啶。体外筛选所有合成的化合物对十二种不同细菌菌株的抗菌活性。已证明这些化合物中的一些对淋病奈瑟氏球菌和金黄色葡萄球菌菌株显示出显着的抗菌活性，与市售的壮观霉素相当甚至更高。