(E)-3-[5-bromo-2-(4-methylpiperazin-1-yl)phenyl]-1-(2-fluoro-4-methoxyphenyl)prop-2-enone | 628322-46-3

• 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: (E)-3-[5-bromo-2-(4-methylpiperazin-1-yl)phenyl]-1-(2-fluoro-4-methoxyphenyl)prop-2-enone
• 英文别名: 3-[5-bromo-2-(4-methyl-piperazin-1-yl)-phenyl]-1-(2-fluoro-4-methoxy-phenyl)-propenone；(E)-3-[5-bromo-2-(4-methylpiperazin-1-yl)phenyl]-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one
• CAS: 628322-46-3
• 化学式: C₂₁H₂₂BrFN₂O₂
• 分子量: 433.32
• InChiKey: ZDKGWLCTBLHLTK-FPYGCLRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-[5-bromo-2-(4-methylpiperazin-1-yl)phenyl]-1-(2-fluoro-4-methoxyphenyl)prop-2-enone 、 3-羟甲基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以18%的产率得到(E)-1-(2-Fluoro-4-methoxy-phenyl)-3-[3'-hydroxymethyl-4-(4-methyl-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：

  5-溴-2-氟苯甲醛 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (E)-3-[5-bromo-2-(4-methylpiperazin-1-yl)phenyl]-1-(2-fluoro-4-methoxyphenyl)prop-2-enone
  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

文献信息

• Quaternary Amino-Function Chalcones
  申请人：Nielsen Simon Feldbaek

  公开号：US20080027075A1

  公开（公告）日：2008-01-31

  The present invention provides novel quaternary amino-functional chalcone derivatives and analogues exhibiting interesting antibacterial activity. The compounds have the general formula (Y 1 ) m —Ar 1 (X 1 )—C(=O)VAr 2 (X 2 )−(Y 2 ) p (I), wherein V designates —CH 2 —CH 2 —, —CH═CH— or —C≡C—; Ar 1 and Ar 2 independently are aryl and heteroaryl; m=0, 1, 2, p=0, 1, 2, m+p>0; each Y 1 and Y 2 independently is -Z—N + (R 1 )(R 2 )R 4 Q − (A); —NR 3 -Z—N + (R 1 )(R 2 )R 4 Q − (B), or —O-Z—N + (R 1 )(R 2 )R 4 Q − (C), R 1 , R 2 , R 3 , R 4 , X 1 , X 2 are substituents, and Q − is an anion. The present invention also relates to the compounds for use as pharmaceutically active agents, in particular against bacterial infections (such as Gram-negative and Gram-positive bacteria, including antibiotic-sensitive or resistant strains), and in the medical treatment of bacterial infections in mammals.
• Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action
  作者：Simon F. Nielsen、Mogens Larsen、Thomas Boesen、Kristian Schønning、Hasse Kromann

  DOI：10.1021/jm049424k

  日期：2005.4.1

  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.