2,5-bis(4-methylpiperazin-1-yl)cyclohexa-2,5-diene-1,4-dione | 321942-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(4-methylpiperazin-1-yl)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,5-bis(4-methylpiperazin-1-yl)-1,4-benzoquinone
• CAS: 321942-59-0
• 化学式: C₁₆H₂₄N₄O₂
• 分子量: 304.392
• InChiKey: JATHJASQHKDZPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 对苯醌 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 6.03h， 以72%的产率得到2,5-bis(4-methylpiperazin-1-yl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones “In-Water” and their biological evaluation as antibacterial and antifungal agents

  摘要：

  Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio) cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa-2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.022

文献信息

• Systematic <i>In Silico</i> Design, Synthesis, and Biological Studies of Some Novel 1,4-Benzoquinone Derivatives for the Prospective Management of Cognitive Decline
  作者：Pragati Silakari、Om Silakari、Poonam Piplani

  DOI：10.1021/acschemneuro.1c00092

  日期：2021.5.5

  Cholinesterases are significant biological targets for the regulation of cholinergic neurotransmission, and their inhibitors are being exploited for the management of cognitive decline in various neurological conditions. The 1,4-benzoquinone scaffold possesses antioxidant potential along with AChE inhibition activity in various neurological disorders. To design novel and potent selective 1,4-benzoquinone

  胆碱酯酶是调节胆碱能神经传递的重要生物学靶标，并且它们的抑制剂正被用于管理各种神经系统疾病中的认知能力下降。1,4-苯醌支架在各种神经系统疾病中具有抗氧化潜力以及AChE抑制活性。为了设计新颖有效的选择性1,4-苯醌类似物作为胆碱酯酶抑制剂，遵循了基于配体的药物设计策略，以开发3D定量结构-选择性关系（QSSR）模型。在最佳拟合模型的基础上，设计并合成了八种新颖的1,4-苯醌衍生物，并采用适当的合成程序进行了表征，并通过各种光谱和元素技术对其进行了表征。使用小鼠脑匀浆作为酶的来源，在不同浓度下的体外乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）抑制潜能。在这些化合物中，以多奈哌齐为参比药物，采用逐步降低的被动回避和逃避学习程序，以0.5 mg / kg的剂量，进一步评估了三种最具选择性的化合物的行为变化。还已经进行了氧化应激标志物（脂质过氧化，超氧化物歧化酶，谷胱甘肽和过氧化氢酶）的生