3-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde | 628325-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde
• CAS: 628325-71-3
• 化学式: C₁₂H₁₅BrN₂O
• 分子量: 283.168
• InChiKey: IBDUKUSJVAXDDW-UHFFFAOYSA-N

物化性质

• 沸点：
  400.5±45.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 18.0h， 生成 (E)-1-[3-[2-(dimethylamino)ethylamino]phenyl]-3-[3-(4-methylpiperazin-1-yl)-5-phenylphenyl]prop-2-en-1-one
  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：

  1-(3-Bromo-5-[1,3]dioxan-2-yl-phenyl)-4-methyl-piperazine 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 3-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde
  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

• Diamino-functional chalcones
  申请人：Nielsen Feldbaek Simon

  公开号：US20060235073A1

  公开（公告）日：2006-10-19

  The invention provides novel diamino-functionalised chalcone derivatives and analogues thereof. Use of the compounds, or compositions comprising them, as pharmaceutically active agents, in particular against bacterial and parasitic infections, is also disclosed. The invention further relates to a method for detecting inhibitory effects against e.g., bacteria, parasites, fungi, and helminths. The chalcones of the invention carry amino substituents and exhibit enhanced biological effects combined with improved metabolic and physicochemical properties, making the compounds useful as drug substances, in particular as antiparasitic and bacteriostatic agents.

  本发明提供了新型二氨基官能化查尔酮衍生物及其类似物。本发明还揭示了将这些化合物或包含它们的组合物用作药物活性剂，特别是用于对抗细菌和寄生虫感染。本发明还涉及一种检测抑制对细菌、寄生虫、真菌和蠕虫等的影响的方法。本发明的查尔酮具有氨基取代基，并表现出增强的生物效应和改善的代谢和物理化学性质，使这些化合物在药物物质中有用，特别是作为抗寄生虫和抗菌剂。
• RHODANINES AND RELATED HETEROCYCLES AS KINASE INHIBITORS
  申请人：HADDACH Mustapha

  公开号：US20100331315A1

  公开（公告）日：2010-12-30

  The invention provides compounds that inhibit PIM kinases and/or CK2, and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, vascular disorders, pathogenic infections and certain immunological disorders.

  该发明提供了能够抑制PIM激酶和/或CK2的化合物以及含有这些化合物的组合物。这些化合物和组合物可用于治疗增殖性疾病如癌症，以及其他与激酶相关的疾病，包括炎症、疼痛、血管疾病、病原体感染和某些免疫性疾病。
• DIAMINO-FUNCTIONAL CHALCONES
  申请人：Lica Pharmaceuticals A/S

  公开号：EP1506158A2

  公开（公告）日：2005-02-16
• US7642367B2
  申请人：——

  公开号：US7642367B2

  公开（公告）日：2010-01-05
• [EN] DIAMINO-FUNCTIONAL CHALCONES<br/>[FR] CHALCONES DIAMINO-FONCTIONNELLES
  申请人：LICA PHARMACEUTICALS AS

  公开号：WO2003097576A2

  公开（公告）日：2003-11-27

  The invention provides novel diamino-functionalised chalcone derivatives and analogues thereof. Use of the compounds, or compositions comprising them, as pharmaceutically active agents, in particular against bacterial and parasitic infections, is also disclosed. The invention further relates to a method for detecting inhibitory effects against e.g., bacteria, parasites, fungi, and helminths. The chalcones of the invention carry amino substituents and exhibit enhanced biological effects combined with improved metabolic and physicochemical properties, making the compounds useful as drug substances, in particular as antiparasitic and bacteriostatic agents.