2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetamide | 557070-88-9

• 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)acetamide
• 英文别名: 2-(4-Oxo-3-phenethyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide；2-[4-oxo-3-(2-phenylethyl)quinazolin-2-yl]sulfanylacetamide
• CAS: 557070-88-9
• 化学式: C₁₈H₁₇N₃O₂S
• mdl: MFCD03429559
• 分子量: 339.418
• InChiKey: DSBKZOHZAQDDGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  4

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)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

• 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.