2-(4-甲基-1-哌嗪基)-4-溴苯甲醛 | 628326-12-5

• 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-(4-甲基-1-哌嗪基)-4-溴苯甲醛
• 中文别名: 4-溴-2-(4-甲基-1-哌嗪)苯甲醛
• 英文名称: 4-bromo-2-(4-methylpiperazin-1-yl)benzaldehyde
• 英文别名: 4-Bromo-2-(4-methylpiperazino)benzaldehyde
• CAS: 628326-12-5
• 化学式: C₁₂H₁₅BrN₂O
• 分子量: 283.168
• InChiKey: NIOICRGSDAAJOW-UHFFFAOYSA-N

物化性质

• 沸点：
  394.0±42.0 °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

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-(4-甲基-1-哌嗪基)-4-溴苯甲醛 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 D(+)-10-樟脑磺酸 作用下， 以 甲苯 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以67%的产率得到7-bromo-2-methyl-1,2,3,4-tetrahydropyrimidin[1,2-a]indole
  参考文献：
  名称：

  钌催化“特权”哌嗪核上的β-C（sp 3）–H功能化

  摘要：

  使用钌催化已经公开了在“特权的”哌嗪核上的β-C（sp 3）-H功能化。提出了钌从邻哌嗪基（杂）芳基醛催化的各种哌嗪稠合的吲哚的催化合成。该转化通过哌嗪的脱氢，然后将瞬时烯胺部分分子内亲核加成到羰基上并进行芳构化级联而发生。

  DOI：

  10.1039/c7cc05604d
• 作为产物：
  描述：

  N-甲基哌嗪 、 4-溴-2-氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以84%的产率得到2-(4-甲基-1-哌嗪基)-4-溴苯甲醛
  参考文献：
  名称：

  钌催化“特权”哌嗪核上的β-C（sp 3）–H功能化

  摘要：

  使用钌催化已经公开了在“特权的”哌嗪核上的β-C（sp 3）-H功能化。提出了钌从邻哌嗪基（杂）芳基醛催化的各种哌嗪稠合的吲哚的催化合成。该转化通过哌嗪的脱氢，然后将瞬时烯胺部分分子内亲核加成到羰基上并进行芳构化级联而发生。

  DOI：

  10.1039/c7cc05604d

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。
• 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.
• 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.