2-amino-4-(N-tosyl-6'-bromo-3'-indolyl)pyrimidine | 289503-27-1

• 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: 2-amino-4-(N-tosyl-6'-bromo-3'-indolyl)pyrimidine
• 英文别名: 4-[6-Bromo-1-(4-methylphenyl)sulfonylindol-3-yl]pyrimidin-2-amine
• CAS: 289503-27-1
• 化学式: C₁₉H₁₅BrN₄O₂S
• 分子量: 443.324
• InChiKey: ZRTSOUNTKPIZMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(N-tosyl-6'-bromo-3'-indolyl)pyrimidine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以76%的产率得到Meridianin D
  参考文献：
  名称：

  Synthesis of Indolylpyrimidines via Cross-Coupling of Indolylboronic Acid with Chloropyrimidines: Facile Synthesis of Meridianin D

  摘要：

  Palladium catalyzed cross-coupling reaction of 3-indolylboronic acid with 2,4-dichloropyrimidines proceeded regioselectively to yield indolyl-or bis(indolyl)pyrimidines in high yield, depending on the projection of 3-indolylboronic acid. The marine indole alkaloid meridianin D and an analogue were synthesised via the palladium catalyzed cross-coupling reaction as a key step.

  DOI：

  10.3987/com-00-8890
• 作为产物：
  描述：

  6-溴-1-甲苯磺酰-1H-吲哚 在 四(三苯基膦)钯 溴 、 叔丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 正戊烷 、 苯 为溶剂， 反应 6.67h， 生成 2-amino-4-(N-tosyl-6'-bromo-3'-indolyl)pyrimidine
  参考文献：
  名称：

  Synthesis of Indolylpyrimidines via Cross-Coupling of Indolylboronic Acid with Chloropyrimidines: Facile Synthesis of Meridianin D

  摘要：

  Palladium catalyzed cross-coupling reaction of 3-indolylboronic acid with 2,4-dichloropyrimidines proceeded regioselectively to yield indolyl-or bis(indolyl)pyrimidines in high yield, depending on the projection of 3-indolylboronic acid. The marine indole alkaloid meridianin D and an analogue were synthesised via the palladium catalyzed cross-coupling reaction as a key step.

  DOI：

  10.3987/com-00-8890

文献信息

• Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria
  作者：William M. Huggins、William T. Barker、James T. Baker、Nicholas A. Hahn、Roberta J. Melander、Christian Melander

  DOI：10.1021/acsmedchemlett.8b00161

  日期：2018.7.12

  In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.
• Synthesis of Indolylpyrimidines via Cross-Coupling of Indolylboronic Acid with Chloropyrimidines: Facile Synthesis of Meridianin D
  作者：Biao Jiang、Cai-guang Yang

  DOI：10.3987/com-00-8890

  日期：——

  Palladium catalyzed cross-coupling reaction of 3-indolylboronic acid with 2,4-dichloropyrimidines proceeded regioselectively to yield indolyl-or bis(indolyl)pyrimidines in high yield, depending on the projection of 3-indolylboronic acid. The marine indole alkaloid meridianin D and an analogue were synthesised via the palladium catalyzed cross-coupling reaction as a key step.