4,5-二乙氧基-2-硝基苯甲酸 | 103796-34-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4,5-二乙氧基-2-硝基苯甲酸
• 英文名称: 2-nitro-4,5-diethoxybenzoic acid
• 英文别名: 4,5-diethoxy-2-nitrobenzoic acid；4,5-diethoxy-2-nitro-benzoic acid；4,5-Diaethoxy-2-nitro-benzoesaeure；Diaethylaether-6-nitro-protocatechusaeure
• CAS: 103796-34-5
• 化学式: C₁₁H₁₃NO₆
• mdl: MFCD11044852
• 分子量: 255.227
• InChiKey: FULLWXSFKCFUCD-UHFFFAOYSA-N

物化性质

• 熔点：
  142-145 ºC
• 密度：
  1.310

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4,5-二乙氧基-2-硝基苯甲酸 在 盐酸 、 草酰氯 、 N,N-二甲基甲酰胺 、 tin(ll) chloride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 (3-Chloro-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine; hydrochloride
  参考文献：
  名称：

  Anilinodialkoxyquinazolines:  Screening Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitors for Potential Tumor Imaging Probes

  摘要：

  The epidermal growth factor receptor (EGFR), a long-standing drug development target, is also a desirable target for imaging. Sixteen dialkoxyquinazoline analogues, suitable for labeling with positron-emitting isotopes, have been synthesized and evaluated in a battery of in vitro assays to ascertain their chemical and biological properties. These characteristics provided the basis for the adoption of a selection schema to identify lead molecules for labeling and in vivo evaluation. A new EGER tyrosine kinase radiometric binding assay revealed that all of the compounds possessed suitable affinity (IC50 = 0.4-51 nM) for the EGFR tyrosine kinase. All of the analogues inhibited ligand-induced EGFR tyrosine phosphorylation (IC50 = 0.8-20 nM). The HPLC-estimated octanol/water partition coefficients ranged from 2 to 5.5. Four compounds, 4-(2'-fluoroanilino)- and 4-(3'-fluoroanilino)-6,7-diethoxyquinazoline as well as 4-(3'chloroanilino)- and 4-(3'-bromoanilino)-6,7-dimethoxyquinazoline, possess the best combination of characteristics that warrant radioisotope labeling and further evaluation in tumor-bearing mice.

  DOI：

  10.1021/jm050607w
• 作为产物：
  描述：

  3,4-二乙氧基甲苯 在 硝酸 、 溶剂黄146 作用下， 生成 4,5-二乙氧基-2-硝基苯甲酸
  参考文献：
  名称：

  Galmarini, Anales des la Asociacion Quimica Argentina, 1951, vol. 39, p. 92,96

  摘要：

  DOI：

文献信息

• Quinazoline derivatives and therapeutic use thereof
  申请人：Lee B. Young

  公开号：US20050187231A1

  公开（公告）日：2005-08-25

  Quinazoline derivatives represented by the general formula pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for using the compounds for treatment of hyperproliferative disorders are also described.

  描述了由一般式表示的喹唑啉衍生物及其药理学可接受的盐，以及含有这些化合物的组合物。还描述了使用这些化合物治疗过度增生性疾病的方法。
• [EN] BENZAMIDE INHIBITORS OF BACTERICAL LIPOPROTEIN SIGNAL PEPTIDASE<br/>[FR] INHIBITEURS DE TYPE BENZAMIDE DE LA PEPTIDASE DU PEPTIDE SIGNAL DES LIPOPROTÉINES BACTÉRIENNES
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2019010165A1

  公开（公告）日：2019-01-10

  Increasing resistance to antibiotics necessitates discovery of new targets and strategies to combat bacteria. Ideal protein targets are required for viability across many species, are unique to prokaryotes to limit effects on the host and have robust assays to quantitate activity and identify novel inhibitors. Lipoprotein signal peptidase (Lsp) is a transmembrane aspartyl protease required for lipoprotein maturation and entirely fits these criteria. We have developed the first in vitro high-throughput assay to monitor proteolysis by Lsp. We employed our HTS assay against 646,275 compounds to discover inhibitors of Lsp and synthesized a range of analogues to generate molecules with nanomolar IC50 values. Importantly, our inhibitors are effective in preventing the growth of E. coli cultures. Our Lsp assay will be a useful tool for biologists to monitor Lsp activity and our inhibitors will facilitate development of antibacterial agents to potentially treat antibiotic-resistant bacteria.

  抗生素的抗性增加使得必须发现新的靶点和策略来对抗细菌。理想的蛋白靶点需要在许多物种中具有生存能力，对原核生物独特，以限制对宿主的影响，并且具有强大的测定活性和识别新型抑制剂的方法。脂蛋白信号肽酶（Lsp）是一种跨膜天冬氨酸蛋白酶，用于脂蛋白成熟，完全符合这些标准。我们开发了第一个体外高通量测定来监测Lsp的蛋白水解作用。我们使用我们的高通量筛选测定对646,275种化合物进行了筛选，以发现Lsp的抑制剂，并合成了一系列类似物，生成具有纳摩尔IC50值的分子。重要的是，我们的抑制剂能够有效地阻止大肠杆菌培养物的生长。我们的Lsp测定将成为生物学家监测Lsp活性的有用工具，我们的抑制剂将有助于开发抗菌剂，可能用于治疗抗生素耐药细菌。
• Quinazoline Derivatives and Therapeutic Use Thereof
  申请人：Lee Young B.

  公开号：US20090030021A1

  公开（公告）日：2009-01-29

  Quinazoline derivatives represented by the general formula pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for using the compounds for treatment of hyperproliferative disorders are also disclosed.

  本发明涉及一般式所代表的喹唑啉衍生物，其药物学上可接受的盐以及含有这些化合物的组合物。还公开了使用这些化合物治疗过度增殖性疾病的方法。
• Szabo; Vinkler, Acta Chimica Academiae Scientiarum Hungaricae, 1958, vol. 17, p. 201,207
  作者：Szabo、Vinkler

  DOI：——

  日期：——
• Lipoprotein Signal Peptidase Inhibitors with Antibiotic Properties Identified through Design of a Robust In Vitro HT Platform
  作者：Seiya Kitamura、Anna Owensby、Daniel Wall、Dennis W. Wolan

  DOI：10.1016/j.chembiol.2017.12.011

  日期：2018.3

  As resistance to antibiotics increases, the exploration of new targets and strategies to combat pathogenic bacteria becomes more urgent. Ideal protein targets are required for viability across many species, are unique to prokaryotes to limit effects on the host, and have robust assays to quantitate activity and identify inhibitors. Lipoprotein signal peptidase (Lsp) is a transmembrane aspartyl protease required for lipoprotein maturation and comprehensively fits these criteria. Here, we have developed the first in vitro high-throughput assay to monitor proteolysis by Lsp. We employed our high-throughput screen assay against 646,275 compounds to discover inhibitors of Lsp and synthesized a range of analogs to generate molecules with nanomolar half maximal inhibitory concentration values. Importantly, our inhibitors are effective in preventing the growth of E. coli cultures in the presence of outermembrane permeabilizer PMBN and should facilitate development of antibacterial agents with a novel mechanism of action to treat antibiotic-resistant bacteria.