4-(3-{(E)-3-[3-(2-Dimethylamino-ethylamino)-phenyl]-3-oxo-propenyl}-3',5'-dimethyl-biphenyl-4-yl)-piperazine-1-carboxylic acid tert-butyl ester | 850790-30-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(3-{(E)-3-[3-(2-Dimethylamino-ethylamino)-phenyl]-3-oxo-propenyl}-3',5'-dimethyl-biphenyl-4-yl)-piperazine-1-carboxylic acid tert-butyl ester
• CAS: 850790-30-6
• 化学式: C₃₆H₄₆N₄O₃
• 分子量: 582.786
• InChiKey: YGQGOSGZMHCYRE-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.12
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(3-{(E)-3-[3-(2-Dimethylamino-ethylamino)-phenyl]-3-oxo-propenyl}-3',5'-dimethyl-biphenyl-4-yl)-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-1-[3-(2-Dimethylamino-ethylamino)-phenyl]-3-(3',5'-dimethyl-4-piperazin-1-yl-biphenyl-3-yl)-propenone
  参考文献：
  名称：

  Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action

  摘要：

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.

  DOI：

  10.1021/jm049424k
• 作为产物：
  描述：

  N-Boc-哌嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-(3-{(E)-3-[3-(2-Dimethylamino-ethylamino)-phenyl]-3-oxo-propenyl}-3',5'-dimethyl-biphenyl-4-yl)-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action

  摘要：

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.

  DOI：

  10.1021/jm049424k