ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 475042-34-3

• 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-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-1,2,3,4-tetrahydro-2- oxopyrimidine-5-carboxylate；ethyl 2-oxo-6-chloromethyl-4-(4-chlorophenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 475042-34-3
• 化学式: C₁₄H₁₄Cl₂N₂O₃
• 分子量: 329.183
• InChiKey: AYKPHOAZINULIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-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-((2-(3-amino-2-cyano-1H-benzo[f]chromen-1-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-4-(4-chlorophenyl)-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 、 4-氯苯甲醛 、 尿素 在 iron(III) oxide 作用下， 以 乙醇 为溶剂， 以98 %的产率得到ethyl 6-(chloromethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  混合相 Fe2O3 纳米棒的绿色合成和表征作为用于 Biginelli 合成的新型磁性可回收非均相催化剂

  摘要：

  以柠檬桉和九里香叶提取物1:1混合物为封端剂，采用溶胶-凝胶自燃法首次成功生物合成了混相（赤铁矿和磁赤铁矿）磁性Fe 2 O 3纳米棒，研究了其对合成 6-(氯甲基)-1,2,3,4-四氢-2-嘧啶酮 (THPMs) 衍生物的催化作用。此外，生物合成的 Fe 2 O 3的相形成、表面形貌和结晶度使用粉末 XRD（X 射线衍射）、UVDRS（紫外-可见反射光谱）、FTIR（傅立叶变换红外光谱）、FESEM（场发射扫描电子显微镜）、EDX（能量色散 X 射线）探索纳米棒 (NR)和 VSM（振动样品磁强计）。此外，研究了生物合成的 Fe 2 O 3 NRs（C1、C2 和 C3）的催化活性，用于一锅法合成乙基 6-(氯甲基)-1,2,3,4-四氢-2-oxo-4 -arylpyrimidine-5-carboxylate通过比吉内利反应。为了实现 6-(氯甲基)-1,2,3,4-四氢-2-嘧啶酮衍生物的高产率

  DOI：

  10.1016/j.molstruc.2023.135246

文献信息

• Design and synthesis of substituted dihydropyrimidinone derivatives as cytotoxic and tubulin polymerization inhibitors
  作者：Sravani Sana、Ramya Tokala、Deepti Madanlal Bajaj、Narayana Nagesh、Kiran Kumar Bokara、Gaddam Kiranmai、Uppu Jaya Lakshmi、Swapna Vadlamani、Venu Talla、Nagula Shankaraiah

  DOI：10.1016/j.bioorg.2019.103317

  日期：2019.12

  were performed. Cell cycle analysis revealed that compound 10f arrested the cells at G2/M phase in a dose-dependent manner. The compound 10f also found to exhibit significant inhibition of tubulin polymerization (IC50 of 6.91 ± 0.43 μM) with microtubule destabilizing properties. Molecular docking studies also revealed that compound 10f efficiently interacted with critical catalytically active residues

  使用操作上简单的Biginelli方案合成新的基于C6-碳的芳基α-卤代丙烯酰胺连接的二氢嘧啶酮衍生物。被评为它们合成的化合物的体外抗增殖潜在对人癌细胞系的一个选定的面板特别是MCF-7（人乳腺癌），MDA-MB-231（人乳腺癌），HCT-116（人结肠癌）， HCT-15（人结肠直肠腺癌），HT-29（人结肠腺癌）和DU145（人前列腺癌）以及正常的肺成纤维细胞（HFL-1）。优选地，发现具有α-卤代丙烯酰胺（10a-g）官能度的化合物表现出最显着的细胞毒性（IC 50列出的癌细胞系，尤其是乳腺癌细胞系MCF-7和MDA-MB-231（IC 50值为0.54±0.12至3.70±0.24 µM）的最大值为0.54±0.12至8.35±0.82 µM）。在合成化合物的接缝中，化合物10f对乳腺癌细胞系MCF-7（IC 50值为0.54±0.12 µM）和MDA-MB-231（IC 50值为1
• A New Discovery towards Novel Skeleton of <scp>Benzimidazole‐Conjugated</scp> Pyrimidinones as Unique Effective Antibacterial Agents
  作者：Xi Yang、Rasheed Syed、Bo Fang、Cheng‐He Zhou

  DOI：10.1002/cjoc.202200326

  日期：2022.11.15

  A class of new potential antibacterial agents with distinctive pyrimidinone benzimidazole skeleton was developed through nucleophilic substitution and Biginelli reaction starting from urea, ethyl 4-chloroacetoacetate and various aldehydes. Some target molecules exhibited strong antibacterial activities, especially pyrimidinone benzimidazole hybrid 9e possessed the strongest inhibitory effects on the

  以尿素、4-氯乙酰乙酸乙酯和多种醛为原料，通过亲核取代和Biginelli反应，开发了一类具有独特嘧啶酮苯并咪唑骨架的新型潜在抗菌剂。部分靶分子表现出较强的抗菌活性，尤其是嘧啶酮苯并咪唑杂合体9e对粪肠球菌和铜绿假单胞菌的生长抑制作用最强，MIC值低于诺氟沙星1 μg/mL。此外，化合物9e对人红细胞表现出很强的抗生物膜能力、低耐药性和优异的生物安全性。进一步的研究表明，化合物9e可能会破坏膜的完整性并导致蛋白质和核酸等细胞成分的泄漏。同时，化合物9e可以降低乳酸脱氢酶活性，阻断细胞代谢，并与DNA发生嵌入相互作用。ADMET 分析预测分子9e具有良好的药代动力学特性和良好的生物利用度特征。
• Synthesis of new polyfunctional 5,6,7,8-tetrahydroimidazo-[1,5-c]pyrimidin-5-ones by the aza-Wittig reaction followed by intramolecular cyclization and 1,3-prototropic shift
  作者：P. S. Lebed’、P. O. Kos、V. V. Polovinko、A. A. Tolmachev、M. V. Vovk

  DOI：10.1134/s1070428009060207

  日期：2009.6

  Ethyl 2-oxo-6-[(triphenyl-lambda(5)-phosphanylidene)aminomethyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylates reacted with organic isocyanates according to the aza-Wittig pattern, and the subsequent intramolecular ring closure and 1,3-H shift resulted in the formation of ethyl 3-alkyl(aryl)amino-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-8-carboxylates.
• 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