ethyl 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetate
• 英文别名: Ethyl-2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetate；ethyl 2-[4-oxo-3-(2-phenylethyl)quinazolin-2-yl]sulfanylacetate
• 化学式: C₂₀H₂₀N₂O₃S
• mdl: MFCD02651096
• 分子量: 368.456
• InChiKey: GFVAGEPPWUXTTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetate 在 肼 作用下， 以 乙醇 为溶剂， 生成 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetohydrazide
  参考文献：
  名称：

  Synthesis, anticancer and apoptosis-inducing activities of quinazoline–isatin conjugates: epidermal growth factor receptor-tyrosine kinase assay and molecular docking studies

  摘要：

  A new series of quinazolinone compounds 16-34 incorporating isatin moieties was synthesized. The antitumor efficacy of the compounds against MDA-MB-231, a breast cancer cell line, and LOVO, a colon cancer cell line, was assessed. Compounds 20, 21, 22, 23, 25, 27, 28, 29, 30, 31, 32, 33, and 34 displayed potent antitumor activity against MDA-MB-231 and LOVO cells (IC50: 10.38-38.67 mu M and 9.91-15.77 mu M, respectively); the comparative IC50 values for 5-fluorouracil and erlotinib in these cells lines were 70.28 mu M, 22.24 mu M and 15.23 mu M, 25.31 mu M respectively. The EGFR-TK assay and induction of apoptosis for compound 31 were investigated to assess its potential cytotoxic activity as a representative example of the novel synthesized compounds. At a concentration of 10 mu M, compound 31 exhibited efficient inhibitory effect against EGFR-TK and induced apoptosis in MDA-MB-231 cells. Furthermore, a molecular docking study for compound 31 and erlotinib was performed to verify the binding mode toward the EGFR kinase enzyme, and showed a similar interaction as that with erlotinib alone.

  DOI：

  10.1080/14756366.2017.1344981
• 作为产物：
  描述：

  2-苯基乙基异硫代氰酸酯 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.0h， 生成 ethyl 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of some novel substituted 2-mercapto-3-phenethylquinazolines as antitumor agents

  摘要：

  A novel series of 2-(substituted thio)-3-phenethylquinazolin-4(3H)-one and 2-([5-mercapto-4-(substituted)-4H-1,2,4-triazol-3-yl)methylthio]-3-phenethylquinazolin-4(3H)-one (1-25) were designed, synthesized, and evaluated for their in vitro antitumor activity. A single dose (10 mu M) of the test compounds was used in the National Cancer Institute (NCI) 60 cell lines panel assay. Compound 2 showed sensible selective activities toward renal and breast cancer cell lines, whereas breast cancer cell lines showed moderate sensitivity to compound 13. At the same time, compound 22 yielded reasonable selective activities toward leukemia and non-small cell lung cancer cell lines. The results achieved can be used as a useful template for future development and further derivatization or modification to obtain more potent and selective antitumor agents.

  DOI：

  10.1007/s00044-013-0546-z

文献信息

• Spectroscopic analysis (FT-IR, FT-Raman and NMR) and molecular docking study of ethyl 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-acetate
  作者：Adel S. El-Azab、K. Jalaja、Alaa A.-M. Abdel-Aziz、Abdulrahman M. Al-Obaid、Y. Sheena Mary、C. Yohannan Panicker、C. Van Alsenoy

  DOI：10.1016/j.molstruc.2016.05.004

  日期：2016.9

  Abstract The vibrational wavenumbers, molecular structure, MEP, NLO, NBO and HOMO, LUMO analysis of Ethyl 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-acetate (EPDA) were reported. The change in electron density in the antibonding orbitals and stabilization energies have been calculated by NBO analysis to give clear evidence of stabilization in the hyperconjugation of hydrogen bonded interaction

  摘要 报道了2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-acetate (EPDA) 的振动波数、分子结构、MEP、NLO、NBO 和HOMO、LUMO 分析。通过 NBO 分析计算了反键轨道中电子密度和稳定能的变化，以提供氢键相互作用超共轭稳定的明确证据。HOMO 和 LUMO 能量的差异支持分子内的电荷转移相互作用。还报告了核磁共振研究和福井函数。从分子静电势图可以看出，负电荷覆盖了羰基、苯环，而正区域在 CH 2 基团上方，带有乙酸酯基团。