ethyl 4-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetamido)benzoate | 443353-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetamido)benzoate
• 英文别名: ethyl-4-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetamido)benzoate；Ethyl 4-(2-{[4-oxo-3-(2-phenylethyl)-3,4-dihydroquinazolin-2-YL]sulfanyl}acetamido)benzoate；ethyl 4-[[2-[4-oxo-3-(2-phenylethyl)quinazolin-2-yl]sulfanylacetyl]amino]benzoate
• CAS: 443353-43-3
• 化学式: C₂₇H₂₅N₃O₄S
• mdl: MFCD05023720
• 分子量: 487.579
• InChiKey: NLKDLTVFXRZUON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

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

• FT-IR, FT-Raman and molecular docking study of ethyl 4-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetamido)benzoate
  作者：Adel S. El-Azab、Y. Sheena Mary、C. Yohannan Panicker、Alaa A.-M. Abdel-Aziz、Ibrahim A. Al-Suwaidan、C. Van Alsenoy

  DOI：10.1016/j.molstruc.2016.01.041

  日期：2016.5

  sulphur atoms and N 3 atom of triazole ring and the maximum positive region is localized on NH group, indicating a possible site for nucleophilic attack. The predicted nonlinear optical properties of the title compound are much greater than that of urea. The molecular docking studies show that the docked ligand, title compound forms a stable complex with pyrrole inhibitor and gives a binding affinity

  摘要 4-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)acetamido)benzoate 的 FT-IR 和 FT-Raman 光谱被记录、分配并与理论结果进行比较。由超共轭相互作用引起的分子的稳定性、电荷离域已经使用自然键轨道分析进行了分析。从分子的优化几何结构、分子静电势、非线性光学性质和标题化合物的前沿分子轨道在 DFT 水平上进行。从分子静电势图中可以看出，最大负区域位于三唑环的硫原子和 N 3 原子上，最大正区域位于 NH 基团上，表明可能存在亲核攻击位点。标题化合物的预测非线性光学性质远大于尿素。分子对接研究表明，对接配体、标题化合物与吡咯抑制剂形成稳定的复合物，结合亲和力值为 -9.5 kcal/mol，该结果表明该化合物可能对吡咯抑制剂表现出抑制活性。