2-溴-5-(4-甲基哌嗪-1-基)苯甲醛 | 628325-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-溴-5-(4-甲基哌嗪-1-基)苯甲醛
• 英文名称: 2-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde
• 英文别名: 2-Bromo-5-(4-methyl-piperazin-1-YL)-benzaldehyde
• CAS: 628325-61-1
• 化学式: C₁₂H₁₅BrN₂O
• 分子量: 283.168
• InChiKey: WDNLRASDXSUTOO-UHFFFAOYSA-N

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

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-溴-5-(4-甲基哌嗪-1-基)苯甲醛 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-[5-(4-methylpiperazin-1-yl)-2-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：

  2-(3-溴苯基)-1,3-二恶烷 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 tris(dibenzylideneacetone)dipalladium (0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.17h， 生成 2-溴-5-(4-甲基哌嗪-1-基)苯甲醛
  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。
• [EN] FUSED TETRACYCLIC COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF IN MEDICINE<br/>[FR] COMPOSÉ TÉTRACYCLIQUE FUSIONNÉ, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION EN MÉDECINE<br/>[ZH] 稠合四环类化合物、其制备方法及其在医药上的应用
  申请人：[en]JIANGSU HENGRUI PHARMACEUTICALS CO., LTD.;[zh]江苏恒瑞医药股份有限公司

  公开号：WO2022199676A1

  公开（公告）日：2022-09-29

  涉及稠合四环类化合物、其制备方法及其在医药上的应用。具体而言，涉及一种通式(I)所示的稠合四环类化合物、其制备方法及含有该类化合物的药物组合物以及其作为治疗剂的用途，特别是其在制备用于抑制HPK1的药物中的用途。其中通式(I)中各基团如说明书中所定义。
• 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.