α-bromo-α′-(4-O-benzophenone)-p-xylene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-bromo-α′-(4-O-benzophenone)-p-xylene
• 英文别名: [4-[[4-(Bromomethyl)phenyl]methoxy]phenyl]-phenylmethanone；[4-[[4-(bromomethyl)phenyl]methoxy]phenyl]-phenylmethanone
• 化学式: C₂₁H₁₇BrO₂
• 分子量: 381.269
• InChiKey: ADOIVUQYOOSBAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-bromo-α′-(4-O-benzophenone)-p-xylene 在 sodium azide 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到4-(4-azidoethylbenzyloxy)benzophenone
  参考文献：
  名称：

  Toward Analogues of MraY Natural Inhibitors: Synthesis of 5′-Triazole-Substituted-Aminoribosyl Uridines Through a Cu-Catalyzed Azide–Alkyne Cycloaddition

  摘要：

  A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the S' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu (1)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.

  DOI：

  10.1021/jo4014035
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 4-羟基-二苯甲酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以44%的产率得到α-bromo-α′-(4-O-benzophenone)-p-xylene
  参考文献：
  名称：

  Toward Analogues of MraY Natural Inhibitors: Synthesis of 5′-Triazole-Substituted-Aminoribosyl Uridines Through a Cu-Catalyzed Azide–Alkyne Cycloaddition

  摘要：

  A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the S' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu (1)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.

  DOI：

  10.1021/jo4014035

文献信息

• 5′-Methylene-triazole-substituted-aminoribosyl uridines as MraY inhibitors: synthesis, biological evaluation and molecular modeling
  作者：Mickaël J. Fer、Ahmed Bouhss、Mariana Patrão、Laurent Le Corre、Nicolas Pietrancosta、Ana Amoroso、Bernard Joris、Dominique Mengin-Lecreulx、Sandrine Calvet-Vitale、Christine Gravier-Pelletier

  DOI：10.1039/c5ob00707k

  日期：——

  Two families of compounds were synthesized from a unique epoxide which was regioselectively opened by acetylide ions (for compounds II) or azide ions (for compounds III). Sequential diastereoselective glycosylation with a ribosyl fluoride derivative, Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) with various complementary azide and alkyne partners afforded the targeted compounds after final deprotection

  描述了5'-亚甲基-[1,4]-三唑取代的氨基核糖基尿苷的直接合成。由独特的环氧化物合成了两族化合物，该环氧化物被乙炔离子（对于化合物II）或叠氮化物离子（对于化合物III）区域选择性地打开。与核糖基氟化物衍生物，Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）以及各种互补的叠氮化物和炔烃配偶体相继进行非对映选择性糖基化反应，最终脱保护后即可得到目标化合物。所得的16种化合物的生物活性以及先前报道的14种化合物的生物活性I评估缺少5'亚甲基的MraY转移酶活性。在30种测试化合物中，有18种化合物显示出MraY抑制，IC 50为15至150μM。进行了分子建模研究，以合理化所观察到的结构-活性关系（SAR），这使我们能够将最有效化合物的活性与涉及MraY AA的Leu191的相互作用相关联。还评估了抗菌活性，七种化合物对革兰氏阳性细菌病原体表现出良好的活性，MIC范围为8至32μgmL
• Toward Analogues of MraY Natural Inhibitors: Synthesis of 5′-Triazole-Substituted-Aminoribosyl Uridines Through a Cu-Catalyzed Azide–Alkyne Cycloaddition
  作者：Mickaël J. Fer、Samir Olatunji、Ahmed Bouhss、Sandrine Calvet-Vitale、Christine Gravier-Pelletier

  DOI：10.1021/jo4014035

  日期：2013.10.18

  A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the S' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu (1)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.