3-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)propanamide | 1443441-41-5

• 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: 3-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)propanamide
• 英文别名: 3-(4-oxo-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)propanamide；3-[4-oxo-3-(2-phenylethyl)quinazolin-2-yl]sulfanyl-N-(3,4,5-trimethoxyphenyl)propanamide
• CAS: 1443441-41-5
• 化学式: C₂₈H₂₉N₃O₅S
• 分子量: 519.621
• InChiKey: CKXUWBLWNRGBTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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 3-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3,4,5-trimethoxyphenyl)propanamide
  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

• Spectroscopic and reactive properties of a newly synthesized quinazoline derivative: Combined experimental, DFT, molecular dynamics and docking study
  作者：Adel S. El-Azab、Y. Shyma Mary、Y. Sheena Mary、C. Yohannan Panicker、Alaa A.-M. Abdel-Aziz、Menshawy A. Mohamed、Stevan Armaković、Sanja J. Armaković、Christian Van Alsenoy

  DOI：10.1016/j.molstruc.2017.01.032

  日期：2017.4

  to investigate the possibility for autoxidation mechanism of the investigated molecule. Molecular dynamics (MD) simulations were used in order to investigate which atoms of the title molecule have the most pronounced interactions with water molecules. Molecular docking studies reveal that the inhibitor forms a stable complex with HNE as is evident from the binding affinity −10.9 kcal/mol and the results

  摘要 3-(4-oxo-phenethyl-3,4-dihydroquinazolin-2-ylthio)-N-(3, 4,5-三甲氧基苯基）丙酰胺通过 B3LYP 理论水平使用 6-311++G(d,p)(5D,7F) 基组进行。实验获得的波数与理论预测的波数一致。从 MEP 图中可以看出，负电荷覆盖了羰基、单取代苯环、O59 原子，正区域位于氮原子和氢原子上方。通过测定一阶和二阶超极化来研究标题分子的 NLO 行为。还报告了分子轨道和分子静电势图。还分析了核磁共振谱和福井指数。通过平均局部电离能 (ALIE)、福井函数和键解离能 (BDE) 的计算确定了从反应性方面来看重要的分子位点。用于提取氢的 BDE 有助于我们研究所研究分子自氧化机制的可能性。使用分子动力学 (MD) 模拟来研究标题分子的哪些原子与水分子的相互作用最明显。分子对接研究表明，该抑制剂与 HNE 形成稳定的复合物，结合亲和力为