ethyl 6-(chloromethyl)-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1150096-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 6-(chloromethyl)-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl-6-(chloromethyl)-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
• CAS: 1150096-23-3
• 化学式: C₁₄H₁₄ClN₃O₅
• 分子量: 339.735
• InChiKey: UCJHGLJNTZAZER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-(chloromethyl)-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 丙酮 、 叔丁醇 为溶剂， 反应 18.0h， 生成 ethyl 6-((4-((4-(3-amino-2-cyano-1H-benzo[f]chromen-1-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Chromene–triazole-pyrimidine based chemosensor therapeutics for the in vivo and in vitro detection of Fe³⁺ ions

  摘要：

  MCR和点击合成选择性和敏感的Fe3+传感器，可以与CDK2蛋白相互作用，并对人类宫颈癌细胞系HeLa的细胞毒性进行开发。

  DOI：

  10.1039/d0nj05697a
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 间硝基苯甲醛 、 尿素 反应 1.0h， 以83%的产率得到ethyl 6-(chloromethyl)-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Chromene–triazole-pyrimidine based chemosensor therapeutics for the in vivo and in vitro detection of Fe³⁺ ions

  摘要：

  MCR和点击合成选择性和敏感的Fe3+传感器，可以与CDK2蛋白相互作用，并对人类宫颈癌细胞系HeLa的细胞毒性进行开发。

  DOI：

  10.1039/d0nj05697a

文献信息

• Synthesis and evaluation of dihydropyrimidinone-derived selenoesters as multi-targeted directed compounds against Alzheimer’s disease
  作者：Flavio A.R. Barbosa、Rômulo F.S. Canto、Sumbal Saba、Jamal Rafique、Antonio L. Braga

  DOI：10.1016/j.bmc.2016.09.031

  日期：2016.11

  describes the synthesis and evaluation of new dihydropyrimidinone (DHPM)-derived selenoesters as potential multi-targeted agents for the treatment of Alzheimer’s disease. A series of DHPM-derived selenoesters were obtained with high structural diversity through a short and modular synthetic route. The antioxidant activity was evaluated by TBARS and iron chelation assays. These compounds were also evaluated

  本文介绍了新的二氢嘧啶酮（DHPM）衍生的硒酸酯的合成和评估，作为潜在的多靶点药物治疗阿尔茨海默氏病。通过短而模块化的合成途径，获得了具有高度结构多样性的一系列DHPM衍生的硒酸酯。通过TBARS和铁螯合测定法评估抗氧化剂活性。这些化合物也被评估为乙酰胆碱酯酶抑制剂（AChEi）。这些化合物具有良好的抗氧化活性，因为它们具有出色的脂质过氧化抑制作用和良好的铁螯合活性。另外，它们显示出乙酰胆碱酯酶抑制活性，并且其中一些表现出优于标准药物加兰他敏的活性。在计算机上的预测表明，化合物1h可能表现出良好的药代动力学特征。因此，本文所述的一系列DHPM衍生的硒酸酯在寻找用于治疗阿尔茨海默氏病的新的多靶点疗法中显示出开发抗氧化剂和抗胆碱酯酶的良好潜力。
• Design, synthesis and evaluation of seleno-dihydropyrimidinones as potential multi-targeted therapeutics for Alzheimer's disease
  作者：Rômulo F. S. Canto、Flavio A. R. Barbosa、Vanessa Nascimento、Aldo S. de Oliveira、Inês M. C. Brighente、Antonio Luiz Braga

  DOI：10.1039/c4ob00598h

  日期：——

  In this paper we report the design, synthesis and evaluation of a series of seleno-dihydropyrimidinones as potential multi-targeted therapeutics for Alzheimer's disease. The compounds show excellent results as acetylcholinesterase inhibitors, being as active as the standard drug. All these compounds also show very good antioxidant activity through different mechanisms of action.

  在本文中，我们报告了一系列硒代-二氢嘧啶酮的设计，合成和评估，它们可作为阿尔茨海默氏病的潜在多靶点疗法。该化合物作为乙酰胆碱酯酶抑制剂表现出优异的结果，其活性与标准药物相同。所有这些化合物还通过不同的作用机理表现出非常好的抗氧化活性。
• Al₂O₃/MeSO₃H: A Novel and Recyclable Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidinones or Their Sulfur Derivatives in Biginelli Condensation
  作者：Hashem Sharghi、Mahboubeh Jokar

  DOI：10.1080/00397910802444258

  日期：2009.2.25

  Al2O3/CH3SO3H (AMA) is an efficient catalyst for the three-component condensation reaction of aldehyde, 1,3-dicarbonyl compound, and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2-(1H)-ones in high isolated yield via this procedure, which works very effectively regardless of the electronic nature of the substituent on the ring, although electron-donating groups precipitate the rate of reaction. The catalyst is recyclable and stable at room temperature, and the reaction protocol is simple, is cost-effective, and gives good isolated yield with high purity.
• In silico and in vitro study of pyrimidones synthesized with ethylenediamine- modified β-cyclodextrin: potential against ESBL E. coli
  作者：Manojkumar Rajapriyan、Javed Masood Khan、Imran Khan R.、Ayyiliath M. Sajith、Syed Ali Padusha M.

  DOI：10.4314/bcse.v38i4.23

  日期：——

  Modern organic synthesis is primarily focused on developing environmentally benign synthetic protocols by employing green chemistry principles. Accordingly, in our recent research work, we herein report the use of modified supramolecular host cyclodextrin as an effective solid based green catalyst for accessing structurally diverse and medicinally relevant pyrimidone architectures. The catalyst and the synthesized compounds 4 (a-r) were characterized using FT-IR, NMR and GC-mass spectroscopy. Major highlights of the reported work include the economical atom process, remarkably gentler reaction conditions, ease of operation, high isolated yields, and excellent catalyst turnover numbers. The molecular docking studies suggest that the compound 4n has hydrogen bonding, hydrophobic and π-pair interactions with the active site of the CXT M 15 receptor. Further, the in-vitro antibacterial study as well as the screening of anti-biofilm activity resulted in a BIC value of 76.79 ± 0.785% at a concentration of 10 µg/mL and morphological alterations induced by DHPMs against the ESBL E. coli strain aggregated with a good result. KEY WORDS: Ethylenediamine modified β-CD, Multicomponent reaction, 3,4-dihydropyrimidin-2(1H)-ones DHPM derivatives, Solvent-free conditions, Reusability, Antibactercidal Bull. Chem. Soc. Ethiop. 2024, 38(4), 1103-1118.                                                           DOI: https://dx.doi.org/10.4314/bcse.v38i4.23