5-bromo-4-(5-phenyl-thiophen-2-yl)-pyrimidine | 1438096-52-6

• 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: 5-bromo-4-(5-phenyl-thiophen-2-yl)-pyrimidine
• 英文别名: 5-Bromo-4-(5-phenyl-2-thienyl)pyrimidine；5-bromo-4-(5-phenylthiophen-2-yl)pyrimidine
• CAS: 1438096-52-6
• 化学式: C₁₄H₉BrN₂S
• 分子量: 317.209
• InChiKey: FLCSBBNUPYWHSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-噻吩硼酸 、 5-bromo-4-(5-phenyl-thiophen-2-yl)-pyrimidine 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.33h， 以56%的产率得到4-(5-phenylthiophen-2-yl)-5-thiophen-2-yl-pyrimidine
  参考文献：
  名称：

  作为一个新的抗分枝杆菌化合物家族，C（4）和/或C（5）噻吩基取代的嘧啶的合成及其与结构-活性的关系

  摘要：

  铃木交叉偶联和亲核氢取代的结合（小号ñH）反应被证明是从市售的5-溴嘧啶合成C（4）和/或C（5）单（噻吩基）和二（噻吩基）取代的嘧啶的简便方法。所有新的嘧啶被发现是在微摩尔浓度的活性在体外针对ħ 37 RV，鸟，terrae，利福平的和异烟肼耐药的菌株结核分枝杆菌。对于这些化合物，已经获得了小鼠急性体内毒性的数据，这些化合物似乎是有希望的抗结核药。

  DOI：

  10.1016/j.ejmech.2015.05.007
• 作为产物：
  描述：

  5-溴嘧啶 、 2-苯基噻吩 以 三氟乙酸 为溶剂， 反应 24.0h， 生成 5-bromo-4-(5-phenyl-thiophen-2-yl)-pyrimidine
  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 structure–activity relationship for C(4) and/or C(5) thienyl substituted pyrimidines, as a new family of antimycobacterial compounds
  作者：Egor V. Verbitskiy、Ekaterina M. Cheprakova、Pavel A. Slepukhin、Marionella A. Kravchenko、Sergey N. Skornyakov、Gennady L. Rusinov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.ejmech.2015.05.007

  日期：2015.6

  Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions proved to be a convenient method for the synthesis of C(4) and/or C(5) mono(thienyl) and di(thienyl) substituted pyrimidines from commercially available 5-bromopyrimidine. All new pyrimidines were found to be active in micromolar concentrations in vitro against H37Rv, avium, terrae, rifampicin

  铃木交叉偶联和亲核氢取代的结合（小号ñH）反应被证明是从市售的5-溴嘧啶合成C（4）和/或C（5）单（噻吩基）和二（噻吩基）取代的嘧啶的简便方法。所有新的嘧啶被发现是在微摩尔浓度的活性在体外针对ħ 37 RV，鸟，terrae，利福平的和异烟肼耐药的菌株结核分枝杆菌。对于这些化合物，已经获得了小鼠急性体内毒性的数据，这些化合物似乎是有希望的抗结核药。
• 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.