2-(3-methoxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one | 1095897-29-2

• 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-(3-methoxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(3-Methoxyphenyl)-3-phenyl-1,2-dihydroquinazolin-4-one
• CAS: 1095897-29-2
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: ZGHFRYBKBCWNMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[(3-methoxyphenyl)methylideneamino]-N-phenylbenzamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以292 mg的产率得到2-(3-methoxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  N-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin

  摘要：

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.

  DOI：

  10.1021/jm4002346

文献信息

• Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
  作者：Yang Yang、Renzhong Fu、Yang Liu、Jing Cai、Xiaojun Zeng

  DOI：10.1016/j.tet.2020.131312

  日期：2020.7

  3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational

  在微波促进下，通过杂多阴离子基离子液体催化的等位酸酐，胺和醛（或酮）通过一锅三组分反应合成了一系列2,3-二氢喹唑啉-4（1 H）-one衍生物。条件。发现该实用方案可耐受具有不同官能团的多种底物。中等至极好的产量，无溶剂介质和操作简便是主要亮点。此外，催化剂可以回收和再利用而没有明显的反应性损失。与现有方法相比，该方法提供了绿色且经过改进的协议。
• 2,3-dihydroquinazolin-4(1H)-one derivatives for use in the treatment of viral infections
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES

  公开号：EP2722047A1

  公开（公告）日：2014-04-23

  Use of 2,3-dihydroquinazolin-4(1H)-one cyclic derivatives of formula (I) for the treatment of infection with viruses entering cells by endocytosis, especially filovirus such as Ebolavirus

  使用2,3-二氢喹唑啉-4(1H)-酮环衍生物（化学式I）治疗通过内吞作用进入细胞的病毒感染，尤其是类似埃博拉病毒的丝状病毒。
• NEW COMPOUNDS HAVING A PROTECTIVE ACTIVITY AGAINST TOXINS WITH INTRACELLULAR ACTIVITY
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES

  公开号：US20150291568A1

  公开（公告）日：2015-10-15

  The present invention concerns a new family of 2,3-dihydroquinazolin-4(1H)-one compounds of general formula (I), and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as ricin or Shiga toxin, for example, using retrograde transport to intoxicate cells.

  本发明涉及一种新的2,3-二氢喹唑啉-4(1H)-酮化合物家族，其一般式为(I)，并将其用作抑制具有细胞内活性的毒素的毒性作用的药物，例如利辛或志贺毒素，通过逆行转运使细胞中毒。
• [EN] 2,3-DIHYDROQUINAZOLIN-4(1 H)-ONE DERIVATIVES FOR USE IN THE TREATMENT OF VIRAL INFECTIONS<br/>[FR] DÉRIVÉS DE 2,3-DIHYDROQUINAZOLINE-4(1H)-ONE DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：COMMISSARIAT ENERGIE ATOMIQUE

  公开号：WO2014060588A1

  公开（公告）日：2014-04-24

  Use of 2,3-dihydroquinazolin-4(lH)-one cyclic derivatives of formula (I) for the treatment of infection with viruses entering cells by endocytosis, especially filovirus such as Ebolavirus.

  使用式(I)的2,3-二氢喹唑啉-4(1H)-酮环衍生物治疗通过内吞作用进入细胞的病毒感染，尤其是埃博拉病毒等丝状病毒。
• Hydroxyapatite nanoparticles (HAP NPs): a green and efficient heterogeneous catalyst for three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media
  作者：Nasrin Razavi、Batool Akhlaghinia

  DOI：10.1039/c5nj02123e

  日期：——

  Hydroxyapatite nanoparticles (HAP NPs) are found to be an efficient catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media via a three-component one-pot condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium salts. The nanocatalyst (characterized by FT-IR, XRD, SEM-EDS and TEM techniques) is easily recyclable six times without the significant

  羟基磷灰石纳米粒子（HAP NPs）被发现是一种有效的催化剂，可通过三酸酐一锅法将Isatoic酐和芳族醛与伯醛缩合，在水介质中合成2,3-二氢喹唑啉-4（1 H）-one衍生物。胺或铵盐。纳米催化剂（通过FT-IR，XRD，SEM-EDS和TEM技术表征）可轻松回收六次，而不会显着降低催化活性。其他显着特征包括官能团耐受性范围广，在温和的反应条件下产物的收率好至极好。