6-fluoro-2-phenylquinazolin-4(3H)-one | 371945-79-8

• 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: 6-fluoro-2-phenylquinazolin-4(3H)-one
• 英文别名: 6-Fluoro-2-phenylquinazolin-4(3H)-one；6-fluoro-2-phenyl-3H-quinazolin-4-one
• CAS: 371945-79-8
• 化学式: C₁₄H₉FN₂O
• 分子量: 240.237
• InChiKey: YBGVJFZTKPJHFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-2-phenylquinazolin-4(3H)-one 在 氯化亚砜 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-anilino-6-fluoro-2-phenylquinazoline
  参考文献：
  名称：

  The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells

  摘要：

  We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal anti-body, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.059
• 作为产物：
  描述：

  2-硝基-5-氟苯甲酰胺 在 palladium 10% on activated carbon 、 氢气 、 sodium hydrogensulfite 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 生成 6-fluoro-2-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells

  摘要：

  We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal anti-body, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.059

文献信息

• 喹唑啉酮衍生物的合成方法
  申请人：南京理工大学

  公开号：CN110357823A

  公开（公告）日：2019-10-22

  本发明公开了一种喹唑啉酮衍生物的合成方法。所述方法以邻氨基苯甲腈类化合物和伯醇为原料，以2,2,6,6‑四甲基哌啶氧化物为催化剂，九水合硝酸铁为助催化剂，空气或氧气作为氧化剂合成喹唑啉酮衍生物。本发明使用廉价易得的邻氨基苯甲腈和伯醇为初始原料，以空气或氧气作为氧化剂，副产物为对环境没有污染的水，绿色环保，反应条件温和，产物的选择性和产率高，具有广阔的工业发展前景。
• Pd-Catalyzed Benzylic C–H Amidation with Benzyl Alcohols in Water: A Strategy To Construct Quinazolinones
  作者：Hidemasa Hikawa、Yukari Ino、Hideharu Suzuki、Yuusaku Yokoyama

  DOI：10.1021/jo301282n

  日期：2012.8.17

  synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C–H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.

  开发了通过邻氨基苯甲酰胺与苄醇的钯催化多米诺反应合成4-苯基喹唑啉酮的新方法。该协议涉及Ñ -benzylation，苄基的C-H酰胺化，和脱氢在水中，这可能在平滑代（η的发挥重要的作用3 -苄基）钯物种通过羟基的苄醇的活化。
• “On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile
  作者：Zibin Liu、Li-Yan Zeng、Chao Li、Fubiao Yang、Fensheng Qiu、Shuwen Liu、Baomin Xi

  DOI：10.3390/molecules23092325

  日期：——

  A versatile and practical “on-water” protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N2. The protocol can be extended

  新开发了一种多功能且实用的“水上”方案，以使用邻溴苯甲腈作为新型起始材料合成喹唑啉酮。研究发现，空气和水在喹唑啉酮的合成中起着重要作用。进一步的研究表明，在 N2 的保护下，可以用该方案制备二氢喹唑啉酮。该协议可以扩展到其他底物，并获得了各种喹唑啉酮和二氢喹唑啉酮。o-溴苯甲酰胺、o-氨基苯甲腈和 o-氨基苯甲酰胺也被评估为起始材料，结果进一步证明了该协议的多功能性，尤其是对二氢喹唑啉酮。
• Palladium-Catalyzed Carbonylative Reactions of 1-Bromo-2-fluorobenzenes with Various Nucleophiles: Effective Combination of Carbonylation and Nucleophilic Substitution
  作者：Jianbin Chen、Kishore Natte、Helfried Neumann、Xiao-Feng Wu

  DOI：10.1002/chem.201405221

  日期：2014.12.1

  A systematic study on the carbonylative transformation of 1‐bromo‐2‐fluorobenzenes with various nucleophiles has been performed. Different types of double nucleophiles, such as NN, NC, OC, and NS, can be effectively applied as coupling partners. The corresponding six‐membered heterocycles were isolated in moderate to good yields.

  对1-溴-2-氟苯与各种亲核试剂的羰基化转化进行了系统的研究。不同类型的双亲核试剂，例如N，N'-  N，N-  C，O  C，和N  S，可以有效地应用作为偶联。相应的六元杂环化合物以中等至良好的收率被分离出来。
• A highly efficient heterogeneous copper-catalyzed cascade reaction of 2-halobenzoic acids and amidines leading to quinazolinones
  作者：Wen He、Hong Zhao、Ruiya Yao、Mingzhong Cai

  DOI：10.1039/c4ra09379h

  日期：——

  The heterogeneous cascade reaction of 2-halobenzoic acids and amidines was achieved in DMF at 60 °C in the presence of 10 mol% of MCM-41-immobilized tridentate nitrogen copper(I) complex [MCM-41-3N–CuI] using Cs2CO3 as base, yielding a variety of quinazolinone derivatives in good to excellent yields. This heterogeneous copper catalyst can be easily prepared from commercially available and inexpensive

  2-卤代苯甲酸和am的级联反应是在60°C的DMF中，使用Cs在10 mol％的MCM-41固定的三齿氮铜（I）络合物[MCM-41-3N–CuI]存在下完成的以2 CO 3为碱，以良好或优异的产率生成各种喹唑啉酮衍生物。这种多相铜催化剂可以容易地由市售和廉价的试剂制备，并通过对反应溶液的简单过滤来回收，并且在不降低活性的情况下重复使用至少10次。