(E)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one | 341998-58-1

• 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: (E)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one
• 英文别名: (E)-1-[6-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-3-(dimethylamino)prop-2-en-1-one
• CAS: 341998-58-1
• 化学式: C₂₀H₁₉BrN₂O₃S
• 分子量: 447.352
• InChiKey: SVXBFWVKSUZSLU-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 反应 16.0h， 生成 4-(6-bromo-1H-indol-3-yl)pyrimidin-2-amine hydrochloride
  参考文献：
  名称：

  Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria

  摘要：

  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.

  DOI：

  10.1021/acsmedchemlett.8b00161
• 作为产物：
  描述：

  6-溴-1-甲苯磺酰-1H-吲哚 在 四氯化锡 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one
  参考文献：
  名称：

  海洋来源的2-氨基嘧啶生物碱水飞蓟素和子午线的合成研究

  摘要：

  描述了9-氨基-4-甲氧基吡啶并[3'，2'：4,5]吡咯并[1,2- c ]嘧啶的九步合成方法，该三环系统存在于海洋生物碱variolins中。天然海洋产品子午线素C–E是从N保护的3-acylindoles开始首次合成的。

  DOI：

  10.1016/s0040-4039(00)00728-0

文献信息

• Synthesis of the indole alkaloids meridianins from the tunicate Aplidium meridianum
  作者：Pilar M Fresneda、Pedro Molina、Juan A Bleda

  DOI：10.1016/s0040-4020(01)00102-8

  日期：2001.3

  The marine natural products meridianins A and C-E have been synthesized for the first time starting from the appropriate N-tosyl-3-acetylindole. A facile two-step conversion of N-tosyl-3-acetylindoles to the corresponding meridianins by treatment with dimethylformamide dimethylacetal and further cyclization of the resulting enaminone with aminoguanidine is described. This method has also been applied for the preparation of the 3-[(2-amino)pyrimidin-4-yl]-7-azaindole. (C) 2001 Elsevier Science Ltd. All rights reserved.