3-(3-氯苯基)-1H-喹唑啉-2,4-二酮 | 2473-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(3-氯苯基)-1H-喹唑啉-2,4-二酮
• 英文名称: 3-(3-chlorophenyl)-2,4(1H,3H)-quinazolinedione
• 英文别名: 3-(3-chlorophenyl)quinazoline-2,4(1H,3H)-dione；3-m-Chlorphenyl-2,4(1H,3H)-chinazolindion；3-(3-Chlor-phenyl)-2,4(1H,3H)-chinazolindion；3-(3-Chlor-phenyl)-2.4-dioxo-1.2.3.4-tetrahydro-chinazolin；3-(3-chloro-phenyl)-1H-quinazoline-2,4-dione；3-(3-Chlor-phenyl)-1H-chinazolin-2,4-dion；3-(3-chloro-phenyl)-2,4-quinazolinedione；3-(3-chlorophenyl)-1H-quinazoline-2,4-dione
• CAS: 2473-93-0
• 化学式: C₁₄H₉ClN₂O₂
• mdl: MFCD01859130
• 分子量: 272.691
• InChiKey: MIOWCSICDLCGIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(3-氯苯基)-1H-喹唑啉-2,4-二酮 、 氯乙酸甲酯 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以49%的产率得到methyl 2-[2,4-dioxo-3-(3-chlorophenyl)-3,4-dihydroquinazolin-1-yl]acetate
  参考文献：
  名称：

  3-aryl(alkyl)quinazoline-2,4(1H,3H)-diones and their alkyl derivatives

  摘要：

  Two-stage reaction of methyl anthranilate with aryl(alkyl) isocyanates in keeping with the quantum-chemical calculations and XRD analysis resulted in 3-aryl(alkyl) quinazoline-2,4(1H,3H)-diones that by treatment with alkyl halides, phenacyl bromides, esters and amides of chloroacetic acid were converted into the corresponding 1-alkyl derivatives.

  DOI：

  10.1134/s1070428009110190
• 作为产物：
  描述：

  间氯苯异氰酸酯 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.5h， 生成 3-(3-氯苯基)-1H-喹唑啉-2,4-二酮
  参考文献：
  名称：

  Specific Inhibitors of Puromycin-Sensitive Aminopeptidase with a 3-(Halogenated Phenyl)-2,4(1H,3H)-quinazolinedione Skeleton

  摘要：

  Specific puromycin-sensitive aminopeptidase (PSA) inhibitors with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton were prepared and their structure-activity relationships were investigated. The nature (F, Cl or Br), number and position(s) of the halogen atom(s) introduced into the 3-phenyl group were concluded to be critical determinants of the inhibitory activity.

  DOI：

  10.3987/com-12-s(n)109

文献信息

• Oxidative Rearrangement of Isatins with Arylamines Using H₂ O₂ as Oxidant: A Facile Synthesis of Quinazoline-2,4-diones and Evaluation of Their Antibacterial Activity
  作者：Guanghao Shi、Xinwei He、Yongjia Shang、Cheng Yang、Liwei Xiang

  DOI：10.1002/cjoc.201700280

  日期：2017.12

  A green and highly efficient synthetic method for the synthesis of quinazoline‐2,4‐diones with hydrogen peroxide as the terminal oxidant has been developed. The reaction features the mild reaction conditions, broad substrate scope, metal‐free catalysts, and sole byproduct water. A plausible mechanism for this process was proposed. Moreover, an antibacterial activity study was performed to evaluate

  开发了一种绿色高效的合成方法，以过氧化氢为末端氧化剂合成喹唑啉-2,4-二酮。该反应具有温和的反应条件，广泛的底物范围，无金属催化剂和唯一的副产物水。为此过程提出了一个合理的机制。此外，还进行了一项抗菌活性研究，以使用肉汤微稀释法评估对两种革兰氏阴性细菌菌株（大肠杆菌和肺炎克雷伯菌）和两种革兰氏阳性细菌菌株（表皮葡萄球菌和金黄色葡萄球菌）的抗菌活性。
• One-pot synthesis of quinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones and 2-thioxoquinazolinones with the aid of low-valent titanium reagent
  作者：Guo-Lan Dou、Man-Man Wang、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.121

  日期：2009.7

  An efficient, convenient, one-pot synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinones was accomplished in good yields via the novel reductive cyclization of ethyl 2-nitrobenzoates with isocyanates or isothiocyanates mediated by TiCl4/Zn system. J. Heterocyclic Chem., (2009).

  通过用TiCl 4 /介导的异氰酸酯或异硫氰酸酯对2-硝基苯甲酸乙酯进行新颖的还原环化反应，可以高效，方便地一锅合成2,4（1 H，3 H）-喹唑啉二酮和2-硫代氧杂喹唑啉酮。锌系统。J.杂环化​​学，（2009）。
• Allosteric inhibitors of hepatitis C virus NS5B polymerase thumb domain site II: Structure-based design and synthesis of new templates
  作者：Savina Malancona、Monica Donghi、Marco Ferrara、Josè I. Martin Hernando、Marco Pompei、Silvia Pesci、Jesus M. Ontoria、Uwe Koch、Michael Rowley、Vincenzo Summa

  DOI：10.1016/j.bmc.2010.03.024

  日期：2010.4

  significant medical problem worldwide. The NS5B Polymerase of HCV plays a central role in virus replication and is a prime target for the discovery of new treatment options. We recently disclosed 1H-benzo[de]isoquinoline-1,3(2H)-diones as allosteric inhibitors of NS5B Polymerase. Structural and SAR information guided us in the modification of the core structure leading to new templates with improved

  慢性丙型肝炎病毒 (HCV) 感染是世界范围内的一个重大医学问题。HCV 的 NS5B 聚合酶在病毒复制中起着核心作用，是发现新治疗方案的主要目标。我们最近公开了 1 H-苯并[ de ] isoquinoline -1,3(2 H )-二酮作为 NS5B 聚合酶的变构抑制剂。结构和 SAR 信息指导我们修改核心结构，从而获得具有改进的活性和毒性/活性窗口的新模板。
• New compounds derived from quinazoline
  申请人：——

  公开号：US20030199530A1

  公开（公告）日：2003-10-23

  A compound selected from those of formula (I): 1 wherein A, B, D, X, R 1 , R 2 , m and n are as defined in the description, their diastereoisomers and addition salts thereof with a pharmaceutically acceptable acid or base.

  从公式（I）中选择的化合物：1其中A，B，D，X，R1，R2，m和n如说明中所定义，它们的对映异构体和与药用可接受酸或碱的加合盐。
• Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered <i>N</i>-Heterocycles
  作者：Karthick Govindan、Alageswaran Jayaram、Tamilselvan Duraisamy、Nian-Qi Chen、Wei-Yu Lin

  DOI：10.1021/acs.joc.2c01026

  日期：2022.7.1

  We disclose a method using phenyl isocyanate to synthesize carbonyl-containing N-heterocycles. The metal-free novel approach for both N–H and C–H carbonylation processes was successfully refined, delivering a range of synthetically valuable derivatives of quinazoline-2,4(1H,3H)-dione, 2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxide, and pyrrolo[1,2-a] quinoxalin-4(5H)-one. The protocol features

  我们公开了一种使用异氰酸苯酯合成含羰基的N-杂环化合物的方法。N-H 和 C-H 羰基化过程的无金属新方法已成功精炼，提供了一系列具有合成价值的喹唑啉-2,4(1 H ,3 H )-二酮、2 H-苯并[ e ] [1,2,4] thiadiazin-3(4 H )-one 1,1-dioxide 和 pyrrolo[1,2 - a ] quinoxalin-4(5 H）-一。该协议具有广泛的底物，具有多种反应，适用于优异的产量、温和的条件和良好的官能团兼容性。此外，该反应的适用性以克级合成和药物分子的合成转化为特征。