2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)acetamide | 1443441-39-1

• 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: 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)acetamide
• 英文别名: 2-[4-oxo-3-(2-phenylethyl)quinazolin-2-yl]sulfanyl-N-(3,4,5-trimethoxyphenyl)acetamide
• CAS: 1443441-39-1
• 化学式: C₂₇H₂₇N₃O₅S
• 分子量: 505.594
• InChiKey: YYZIKUYNPMRVIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 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 2.0h， 生成 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)acetamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 2-mercapto-3-phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study

  摘要：

  A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio) acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI(50) values of 3.16 and 22.60 mu M, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI(50) = 1.77 mu M), colon cancer (GI(50) = 2.02 mu M), non-small cell lung cancer (GI(50) = 2.04 mu M), breast cancer (GI(50) = 2.77 mu M), ovarian cancer (GI(50) = 2.55 mu M) and melanoma cancer (GI(50) = 3.30 mu M). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.056

文献信息

• DFT and experimental (FT-IR and FT-Raman) investigation of vibrational spectroscopy and molecular docking studies of 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl) acetamide
  作者：Adel S. El-Azab、Y. Sheena Mary、C. Yohannan Panicker、Alaa A.-M. Abdel-Aziz、Magda A. El-Sherbeny、C. Van Alsenoy

  DOI：10.1016/j.molstruc.2016.02.038

  日期：2016.6

  comprehensive structural and vibrational study of 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl) acetamide is reported. FT-IR and FT-Raman wavenumbers were compared with the theoretical values obtained from DFT calculations. Theoretical values agree well with the experimental values. Molecular electrostatic potential, frontier molecular orbital analysis and nonlinear

  摘要报道了 2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl) 乙酰胺的综合结构和振动研究。FT-IR 和 FT-拉曼波数与从 DFT 计算获得的理论值进行了比较。理论值与实验值吻合良好。使用理论计算研究了分子静电势、前沿分子轨道分析和非线性光学特性。自然键轨道分析表明，σ* 和 π* 反键轨道中电子密度的电荷和 E(2) 能量证实了分子内分子间电荷转移的发生。通过预测一阶和二阶超极化参数也观察到非线性光学特性。从标题分子的分子静电势图中可以看出，负区主要位于羰基和单取代苯环上，最大的正区位于NH和氢原子上。分子对接结果表明对接的配体标题化合物与 BRCA2 复合物形成稳定的复合物，结合亲和力值为 -7.6 kcal/mol，结果表明该化合物可能对 BRCA2 复合物表现出抑制活性。
• Design, synthesis and biological evaluation of 2-mercapto-3-phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study
  作者：Ibrahim A. Al-Suwaidan、Amer M. Alanazi、Alaa A.-M. Abdel-Aziz、Menshawy A. Mohamed、Adel S. El-Azab

  DOI：10.1016/j.bmcl.2013.04.056

  日期：2013.7

  A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio) acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI(50) values of 3.16 and 22.60 mu M, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI(50) = 1.77 mu M), colon cancer (GI(50) = 2.02 mu M), non-small cell lung cancer (GI(50) = 2.04 mu M), breast cancer (GI(50) = 2.77 mu M), ovarian cancer (GI(50) = 2.55 mu M) and melanoma cancer (GI(50) = 3.30 mu M). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib. (c) 2013 Elsevier Ltd. All rights reserved.