6-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one | 1030524-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 6-Chloro-2-(4-methylphenyl)-3,1-benzoxazin-4-one
• CAS: 1030524-56-1
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: CSTBUAYYURBWTO-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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one 在 劳森试剂 、 一水合肼 、 formamide 、 potassium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 22.0h， 生成 9-chloro-5-p-tolyl-[1,2,4]triazolo[4,3-c]quinazoline-3-thiol
  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
• 作为产物：
  描述：

  5-chloro-2-(4-methylbenzamido)benzoic acid 在 乙酸酐 作用下， 反应 3.0h， 以89%的产率得到6-chloro-2-(p-tolyl)-4H-benzo[d][1,3]oxazin-4-one
  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

• Copper-Catalyzed C-N, C-O Coupling Reaction of Arylglyoxylic Acids with Isatins
  作者：Rashmi Prakash、Sanjib Gogoi

  DOI：10.1002/adsc.201600516

  日期：2016.10.6

  The copper(II)‐catalyzed decarboxylative coupling reactions of arylglyoxylic acids with isatins afford 4H‐benzo[d][1,3]oxazin‐4‐ones via decarbonylation and concurrent C–N, C–O bond formation.

  芳基乙醛酸与Isatin的铜（II）催化的脱羧偶联反应通过脱羰作用和同时的C–N，C–O键形成提供4 H-苯并[ d ] [1,3]恶嗪-4-酮。
• <i>o</i>-Acetoxylation of oxo-benzoxazines <i>via</i> C–H activation by palladium(<scp>ii</scp>)/aluminium oxide
  作者：Ramanand Prajapati、Ajay Kant Gola、Amrendra Kumar、Shubham Jaiswal、Narender Tadigoppula

  DOI：10.1039/d2nj00134a

  日期：——

  Direct activation of sp2 C–H bonds by a palladium catalyst has received significant attention in organic chemistry. However, most of these C–H activation reactions are carried out in hazardous solvents. Herein we report a novel solvent-free direct sp2 C–H bond functionalization (oxygenation) method using Pd(II)/Al2O3 catalysis of oxo-benzoxazine derivatives with good to excellent yields, and demonstrate

  钯催化剂直接活化sp 2 C-H键在有机化学中受到了广泛关注。然而，大多数这些 C-H 活化反应是在危险溶剂中进行的。在此，我们报道了一种使用 Pd( II )/Al 2 O 3催化氧代苯并恶嗪衍生物的新型无溶剂直接 sp 2 C-H 键官能化（氧化）方法，并证明了其在合成药学上重要的化合物。
• Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
  作者：Subir Panja、Srabani Maity、Biju Majhi、Brindaban C. Ranu

  DOI：10.1002/ejoc.201900935

  日期：2019.9.8

  An efficient procedure for the Pd‐catalyzed olefination of 4H‐benzo[d][1,3]oxazin‐4‐ones with activated alkenes has been achieved via C‐H activation. The site selectivity of the reaction was explained by a DFT study.

  通过C-H活化，实现了有效的Pd催化4H-苯并[d] [1,3]恶嗪-4-烯与活化烯烃的烯化反应。DFT研究解释了反应的位点选择性。
• 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）。