2-(4-氧代-3,4-二氢喹唑啉-2-基)乙酸乙酯 | 21419-63-6

• 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: 2-(4-氧代-3,4-二氢喹唑啉-2-基)乙酸乙酯
• 英文名称: ethyl (4-oxo-3,4-dihydroquinazolin-2-yl)acetate
• 英文别名: ethyl 2-(4-oxo-3H-quinazolin-2-yl)acetate；(4-oxo-3,4-dihydro-quinazolin-2-yl)-acetic acid ethyl ester；(4-Oxo-3,4-dihydro-chinazolin-2-yl)-essigsaeure-aethylester；Ethyl 2-(4-oxo-3,4-dihydroquinazolin-2-yl)acetate
• CAS: 21419-63-6
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: GURSKCGVYASDGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(4-氧代-3,4-二氢喹唑啉-2-基)乙酸乙酯 在 肼 作用下， 生成 (4-oxo-3,4-dihydro-quinazolin-2-yl)-acetic acid hydrazide
  参考文献：
  名称：

  Manufacture of photographic color images

  摘要：

  公开号：

  US02668112A1
• 作为产物：
  描述：

  2-(bromomethyl)-4(3H)-quinazolinone 在 水 、 乙酰氯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-(4-氧代-3,4-二氢喹唑啉-2-基)乙酸乙酯
  参考文献：
  名称：

  Chemical Probes to Study ADP-Ribosylation: Synthesis and Biochemical Evaluation of Inhibitors of the Human ADP-Ribosyltransferase ARTD3/PARP3

  摘要：

  The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl]propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of SS compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.

  DOI：

  10.1021/jm401394u

文献信息

• 3-(1,1-Dioxo-2<i>H</i>-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1<i>H</i>)-quinolinones, Potent Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Rosanna Tedesco、Antony N. Shaw、Ramesh Bambal、Deping Chai、Nestor O. Concha、Michael G. Darcy、Dashyant Dhanak、Duke M. Fitch、Adam Gates、Warren G. Gerhardt、Dina L. Halegoua、Chao Han、Glenn A. Hofmann、Victor K. Johnston、Arun C. Kaura、Nannan Liu、Richard M. Keenan、Juili Lin-Goerke、Robert T. Sarisky、Kenneth J. Wiggall、Michael N. Zimmerman、Kevin J. Duffy

  DOI：10.1021/jm050855s

  日期：2006.2.1

  Recently, we disclosed a new class of HCV polymerase inhibitors discovered through high-throughput screening (HTS) of the GlaxoSmithKline proprietary compound collection. This interesting class of 3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones potently inhibits HCV polymerase enzymatic activity and inhibits the ability of the subgenomic HCV replicon to replicate in Huh-7 cells. This report will focus on the structure-activity relationships (SAR) of substituents on the quinolinone ring, culminating in the discovery of 1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone (130), an inhibitor with excellent potency in biochemical and cellular assays possessing attractive molecular properties for advancement as a clinical candidate. The potential for development and safety assessment profile of compound 130 will also be discussed.
• EP2264105
  申请人：——

  公开号：——

  公开（公告）日：——
• Dave, K. G.; Shishoo, G. J.; Devani, M. B., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1497 - 1500
  作者：Dave, K. G.、Shishoo, G. J.、Devani, M. B.、Kalyanaraman, R.、Ananthan, S.、et. al.

  DOI：——

  日期：——
• Cyclic amidines. Part II. Derivatives of 2-amino-4-hydroxyquinoline
  作者：R. Hardman、M. W. Partridge

  DOI：10.1039/jr9540003878

  日期：——
• Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases
  作者：Mahmud Tareq Hassan Khan、Rasool Khan、Yimingjiang Wuxiuer、Mohammad Arfan、Manzoor Ahmed、Ingebrigt Sylte

  DOI：10.1016/j.bmc.2010.04.083

  日期：2010.6.15

  A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 mu M (compound 3) to 122,637 mu M (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 mu M) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 mu M) were found to be the most potent inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.