6-chloro-2-p-tolylquinazolin-4(3H)-thione | 1246524-02-6

• 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: 6-chloro-2-p-tolylquinazolin-4(3H)-thione
• 英文别名: 6-chloro-2-(4-methylphenyl)-1H-quinazoline-4-thione
• CAS: 1246524-02-6
• 化学式: C₁₅H₁₁ClN₂S
• 分子量: 286.785
• InChiKey: JREOBWJMPMKWQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-2-p-tolylquinazolin-4(3H)-thione 在 一水合肼 作用下， 反应 3.0h， 以76%的产率得到6-chloro-4-hydrazinyl-2-p-tolylquinazoline
  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
• 作为产物：
  描述：

  6-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one 在 劳森试剂 、 formamide 作用下， 以 甲苯 为溶剂， 反应 9.0h， 生成 6-chloro-2-p-tolylquinazolin-4(3H)-thione
  参考文献：
  名称：

  一些新型取代喹唑啉类抗肿瘤药的设计，合成及生物学评价

  摘要：

  一种新型系列6-氯-2- p -tolylquinazolinone和取代的- （4-甲基苯甲酰氨基）苯甲酰胺（1 - 20）设计，合成并评价了它们的体外抗肿瘤活性。化合物3、14和16具有显着的广谱抗肿瘤活性。发现化合物16是肾癌（GI 50  = 4.07μM），中枢神经系统癌（GI 50  = 7.41μM），卵巢癌（GI 50  = 7.41μM）和非小细胞肺癌（ GI 50  = 7.94μM）。化合物16的效力高出近1.5倍（平均GI50  = 15.8μM），而5-FU（平均GI 50  = 22.6μM）。

  DOI：

  10.1016/j.ejmech.2014.04.029

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.
• Design, synthesis and biological evaluation of some novel substituted quinazolines as antitumor agents
  作者：Amer M. Alanazi、Alaa A.-M. Abdel-Aziz、Ibrahim A. Al-Suwaidan、Sami G. Abdel-Hamide、Taghreed Z. Shawer、Adel S. El-Azab

  DOI：10.1016/j.ejmech.2014.04.029

  日期：2014.5

  A novel series of 6-chloro-2-p-tolylquinazolinone and substituted-(4-methylbenzamido)benzamide (1–20) were designed, synthesized and evaluated for their in-vitro antitumor activity. Compounds 3, 14 and 16 possessed remarkable broad-spectrum antitumor activity. Compound 16 was found to be a particularly active growth inhibitor of the renal cancer (GI50 = 4.07 μM), CNS cancer (GI50 = 7.41 μM), ovarian

  一种新型系列6-氯-2- p -tolylquinazolinone和取代的- （4-甲基苯甲酰氨基）苯甲酰胺（1 - 20）设计，合成并评价了它们的体外抗肿瘤活性。化合物3、14和16具有显着的广谱抗肿瘤活性。发现化合物16是肾癌（GI 50  = 4.07μM），中枢神经系统癌（GI 50  = 7.41μM），卵巢癌（GI 50  = 7.41μM）和非小细胞肺癌（ GI 50  = 7.94μM）。化合物16的效力高出近1.5倍（平均GI50  = 15.8μM），而5-FU（平均GI 50  = 22.6μM）。