2-(6-chloro-2-p-tolylquinazolin-4-ylthio)-N-phenylacetamide | 1246524-20-8

• 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-(6-chloro-2-p-tolylquinazolin-4-ylthio)-N-phenylacetamide
• 英文别名: 2-[6-chloro-2-(4-methylphenyl)quinazolin-4-yl]sulfanyl-N-phenylacetamide
• CAS: 1246524-20-8
• 化学式: C₂₃H₁₈ClN₃OS
• 分子量: 419.934
• InChiKey: YKBYWBQBGMYHNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-chloro-2-p-tolylquinazolin-4(3H)-thione 、 2-氯乙酰苯胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以88%的产率得到2-(6-chloro-2-p-tolylquinazolin-4-ylthio)-N-phenylacetamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking study

  摘要：

  Novel derivatives of quinazoline (1-27) have been synthesized and tested for their antitumor activity against three tumor cell lines among these cell lines the human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. All tested compounds showed potent and selective activity against breast cancer (MCF-7) with IC50 range of 3.35-6.81 mu g/ml. With regarding broad-spectrum activity compounds 5, 9, 15, 18 and 20 exploited potent antitumor against human liver cell line (HEPG2), human breast cell line (MCF-7) and human cervix cell line (HELA) with IC50 range of 3.35-5.59 mu g/ml. Virtual screening was carried out through docking the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) to predict if these compounds have analogous binding mode to the EGFR inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.06.013

文献信息

• Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking study
  作者：Adel S. El-Azab、Mohamed A. Al-Omar、Alaa A.-M. Abdel-Aziz、Naglaa I. Abdel-Aziz、Magda A.-A. El-Sayed、Abdulaziz M. Aleisa、Mohamed M. Sayed-Ahmed、Sami G. Abdel-Hamide

  DOI：10.1016/j.ejmech.2010.06.013

  日期：2010.9

  Novel derivatives of quinazoline (1-27) have been synthesized and tested for their antitumor activity against three tumor cell lines among these cell lines the human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. All tested compounds showed potent and selective activity against breast cancer (MCF-7) with IC50 range of 3.35-6.81 mu g/ml. With regarding broad-spectrum activity compounds 5, 9, 15, 18 and 20 exploited potent antitumor against human liver cell line (HEPG2), human breast cell line (MCF-7) and human cervix cell line (HELA) with IC50 range of 3.35-5.59 mu g/ml. Virtual screening was carried out through docking the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) to predict if these compounds have analogous binding mode to the EGFR inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.