3-ethyl-6-nitro-3H-quinazolin-4-one | 78875-00-0

• 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: 3-ethyl-6-nitro-3H-quinazolin-4-one
• 英文别名: 3-ethyl-6-nitroquinazolin-4(3H)-one；3-ethyl-6-nitro-3H-quinazolin-4-one；3-Aethyl-6-nitro-3H-chinazolin-4-on；3-ethyl-6-nitroquinazolin-4-one
• CAS: 78875-00-0
• 化学式: C₁₀H₉N₃O₃
• mdl: MFCD08257908
• 分子量: 219.2
• InChiKey: YGHZIYFKMZBUQU-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  399.3±44.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethyl-6-nitro-3H-quinazolin-4-one 在 palladium on activated charcoal 吡啶 、 copper(l) iodide 、 溴 、 甲酸铵 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 8-ethyl-9-oxo-8,9-dihydrothiazolo[5,4-f]quinazoline-2-carbonitrile
  参考文献：
  名称：

  Thiazolo[5,4-f]quinazolin-9-ones, inhibitors of glycogen synthase kinase-3

  摘要：

  In an effort to identify new protein kinase inhibitors with increased potency and selectivity, we have developed the microwave-assisted synthesis of thiazolo[5,4-f]quinazolin-9-ones. The effects of eighteen derivatives on CDK1/cyclin B, CDK5/p25, and GSK-3 were investigated. Several turned out to inhibit GSK-3 in the micromolar range. Molecular modeling studies suggest that the most selective GSK-3 inhibitors 7a-d bind into the ATP-binding site through a key hydrogen bond interaction with Val135 and target the specific hydrophobic backpocket of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.006
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 硝酸 作用下， 生成 3-ethyl-6-nitro-3H-quinazolin-4-one
  参考文献：
  名称：

  Bogert; Geiger, Journal of the American Chemical Society, 1912, vol. 34, p. 532

  摘要：

  DOI：

文献信息

• [EN] FUSED IMIDAZOLE COMPOUNDS<br/>[FR] COMPOSÉS D'IMIDAZOLE CONDENSÉS
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2015115673A1

  公开（公告）日：2015-08-06

  The present invention provides compounds represented by formula (I), pharmaceutically acceptable salts thereof, N-oxides thereof, solvates thereof or prodrugs thereof (wherein the characters are as defined in the description). The compounds represented by formula (I) have affinity and selectivity for the gamma-aminobutyric acid A receptor subunit alpha 5 (GABAA α5) and act as GABAA α5 negative allosteric modulators (GABAA α5 NAM), so that they are useful in the prevention and/or treatment of diseases which are related to the GABAA α5 such as Alzheimer's disease.

  本发明提供了由式(I)表示的化合物，其药学上可接受的盐，N-氧化物，溶剂合物或前药（其中字符如描述中所定义）。由式(I)表示的化合物对γ-氨基丁酸A受体亚单位α5（GABAA α5）具有亲和力和选择性，并作为GABAA α5负向变构调节剂（GABAA α5 NAM）发挥作用，因此它们在预防和/或治疗与GABAA α5相关的疾病，如阿尔茨海默病中是有用的。
• [EN] QUINAZOLINONES DERIVATIVES FOR TREATMENT OF NON-ALCOHOLIC FATTY LIVER DISEASE, PREPARATION AND USE THEREOF<br/>[FR] DÉRIVÉS DE QUINAZOLINONES POUR LE TRAITEMENT DE LA STÉATOSE HÉPATIQUE NON ALCOOLIQUE, LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2022003712A1

  公开（公告）日：2022-01-06

  The present invention described herein relates to a compound having Structure I for treating diseases and disorders for which inhibition or modulation of the Ubiquitin Ligase COP1 enzyme produces a physiologically beneficial response, in particular for the treatment of Non-Alcoholic Fatty Liver Disease (NAFLD). These compounds having Structure I arecapable of increasing the level of adipose triglyceride lipase (ATGL). Also provided is the process of preparing compounds having Structure I.

  本发明描述了一种具有结构I的化合物，用于治疗通过抑制或调节泛素连接酶COP1酶产生生理上有益反应的疾病和紊乱，特别是用于治疗非酒精性脂肪肝病（NAFLD）。这些具有结构I的化合物能够增加脂肪三酸甘油酯脂解酶（ATGL）的水平。还提供了制备具有结构I的化合物的方法。
• Fused imidazole compounds
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US10016439B2

  公开（公告）日：2018-07-10

  The present invention provides compounds represented by formula (I), pharmaceutically acceptable salts thereof, N-oxides thereof, solvates thereof or prodrugs thereof (wherein the characters are as defined in the description). The compounds represented by formula (I) have affinity and selectivity for the gamma-aminobutyric acid A receptor subunit alpha 5 (GABAA α5) and act as GABAA α5 negative allosteric modulators (GABAA α5 NAM), so that they are useful in the prevention and/or treatment of diseases which are related to the GABAA α5 such as Alzheimer's disease.

  本发明提供了式(I)代表的化合物、其药学上可接受的盐、其N-氧化物、其溶液剂或其原药（其中特征如描述中所定义）。式（I）代表的化合物对γ-氨基丁酸A受体亚基α5（GABAA α5）具有亲和性和选择性，可作为GABAA α5负异位调节剂（GABAA α5 NAM），因此可用于预防和/或治疗与GABAA α5相关的疾病，如阿尔茨海默病。
• Novel 9-oxo-thiazolo[5,4-f]quinazoline-2-carbonitrile derivatives as dual cyclin-dependent kinase 1 (CDK1)/glycogen synthase kinase-3 (GSK-3) inhibitors: Synthesis, biological evaluation and molecular modeling studies
  作者：Cédric Logé、Alexandra Testard、Valérie Thiéry、Olivier Lozach、Mélina Blairvacq、Jean-Michel Robert、Laurent Meijer、Thierry Besson

  DOI：10.1016/j.ejmech.2007.09.020

  日期：2008.7

  Continuous efforts in microwave-assisted synthesis and the structure-activity relationships' (SARs) studies of novel modified 9-oxo-thiazolo[5,4-f]quinazoline-2-carbonitriles, allowed identification of new amidine and imidate derivatives as potent and dual CDK1/GSK-3 inhibitors. Combination of lead optimization and molecular modeling studies allowed identification of a dual CDK1/GSK-3 inhibitor (compound 13d) with submicromolar values. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Discovery and Development of Quinazolinones and Quinazolinediones for Ameliorating Nonalcoholic Fatty Liver Disease (NAFLD) by Modulating COP1-ATGL Axis
  作者：Dipayan Sarkar、Saheli Chowdhury、Sunny Goon、Abhishek Sen、Uddipta Ghosh Dastidar、Mohabul Alam Mondal、Partha Chakrabarti、Arindam Talukdar

  DOI：10.1021/acs.jmedchem.3c01431

  日期：2023.12.28