162012-69-3

Basic information

• Product Name: 7-Fluoro-6-nitro-4-hydroxyquinazoline
• Synonyms: 4(1H)-QUINAZOLINONE, 7-FLUORO-6-NITRO-;7-FLUORO-6-NITRO-4-HYDROXY-QUINAZOLINE;7-FLUORO-6-NITRO QUINAZOLINONE;7-Fluoro-6-Nitro-4(H)-Quinazoline;6-Nitro-7-Fluoro-4-HydroxyQuinazoline;7-fluoro-6-nitroquinazolin-4(1H)-one;7-Fluoro-6-nitro-1H-quina...;7-fluoro-6-nitroquinazolin-4-ol
• CAS NO: 162012-69-3
• Molecular Formula: C₈H₄FN₃O₃
• Molecular Weight: 209.13
• EINECS: 1308068-626-2
• Product Categories: Intermediate
• Mol File: 162012-69-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 282-285 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 407.6 °C at 760 mmHg
• Flash Point: 200.3 °C
• Appearance: /
• Density: 1.75 g/cm³
• Vapor Pressure: 7.46E-07mmHg at 25°C
• Refractive Index: 1.713
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.69±0.20(Predicted)
• CAS DataBase Reference: 7-Fluoro-6-nitro-4-hydroxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Fluoro-6-nitro-4-hydroxyquinazoline(162012-69-3)
• EPA Substance Registry System: 7-Fluoro-6-nitro-4-hydroxyquinazoline(162012-69-3)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 162012-69-3(Hazardous Substances Data)

Usage

Description

7-Fluoro-6-nitro-4-hydroxyquinazoline is a chemical compound characterized by its fluoro and nitro functional groups, as well as a hydroxyl group attached to its quinazoline core structure. 7-Fluoro-6-nitro-4-hydroxyquinazoline is known for its potential applications in the pharmaceutical industry, particularly in the development of kinase inhibitors.

Uses

Used in Pharmaceutical Industry:
7-Fluoro-6-nitro-4-hydroxyquinazoline is used as an intermediate in the synthesis of kinase inhibitors, specifically targeting the ATP binding site of the tyrosine kinase activity associated with the epidermal growth factor receptor (EGFR). This application is significant because the inhibition of EGFR tyrosine kinase activity has been shown to be effective in treating various types of cancer, including non-small cell lung cancer, head and neck cancer, and colorectal cancer.
The compound's role in the development of kinase inhibitors is crucial, as these inhibitors can modulate cellular signaling pathways involved in cell proliferation, differentiation, and survival. By targeting the ATP binding site, these inhibitors can disrupt the enzymatic activity of the kinase, thereby potentially slowing down or stopping the progression of cancer cells.

InChI:InChI=1/C8H4FN3O3/c9-5-2-6-4(1-7(5)12(14)15)8(13)11-3-10-6/h1-3H,(H,10,11,13)

Upstream product

• 16499-57-3 7-fluoro-3H-quinazolin-4-one 
• 446-32-2 4-fluoroanthranilic acid 
• 1194097-41-0 2-amino-4-fluoro-5-nitrobenzoic acid 
• 77287-34-4 formamide 
• 16499-57-3 7-fluoro-3,4-dihydroquinazolin-4-one 

Downstream Products

• 936954-09-5 7-ethoxy-6-nitroquinazolin-4-ol 
• 1363358-72-8 N-[4-(3-chloro-4-fluorophenylamino)-7-(8-methyl-8-azabicyclo[3.2.1]octan-3-yloxy)quinazolin-6-yl]-acrylamide 
• 1363359-62-9 N-(4-(3-chloro-4-fluorophenyl))-7-(8-methyl-8-azabicyclo[3.2.1]octan-3-yloxy)quinazolin-4,6-diamine 
• 1363359-61-8 N-(4-(3-chloro-4-fluorophenyl))-7-(8-methyl-8-azabicyclo[3.2.1]octan-3-yloxy)-6-nitroquinazolin-4-amine 
• 1363569-76-9 (E)-N-[7-(7-oxabicyclo[2.2.1]heptan-2-yloxy)-4-(3-chloro-4-fluorophenylamino)quinazolin-6-yl]-4-(piperidin-1-yl)-2-butenamide 
• 1363569-80-5 (E)-N-[7-(7-oxabicyclo[2.2.1]heptan-2-yloxy)-4-(3-chloro-4-fluorophenylamino)quinazolin-6-yl]-4-bromo-2-butenamide 
• 1363359-58-3 7-(7-oxabicyclo[2.2.1]heptan-2-yloxy)-N-(4-(3-chloro-4-fluorophenyl))quinazolin-4,6-diamine 
• 1363359-57-2 7-(7-oxabicyclo[2.2.1]heptan-2-yloxy)-N-(4-(3-chloro-4-fluorophenyl))-6-nitroquinazolin-4-amine 
• 1363569-75-8 (E)-N-[7-(8-oxabicyclo[3.2.1]octan-3-yloxy)-4-(3-chloro-4-fluorophenylamino)quinazolin-6-yl]-4-(piperidin-1-yl)-2-butenamide 
• 1363569-79-2 (E)-N-[7-(8-oxabicyclo[3.2.1]octan-3-yloxy)-4-(3-chloro-4-fluorophenylamino)quinazolin-6-yl]-4-bromo-2-butenamide 
• 1363359-56-1 7-(8-oxabicyclo[3.2.1]octan-3-yloxy)-N-(4-(3-chloro-4-fluorophenyl))quinazolin-4,6-diamine 
• 1363359-55-0 7-(8-oxabicyclo[3.2.1]octan-3-yloxy)-N-(4-(3-chloro-4-fluorophenyl))-6-nitroquinazolin-4-amine 
• 1363358-87-5 N-[4-(3-chloro-4-fluorophenylamino)-7-(2-(7-methyl-7-azaspiro[3.5]nonan-2-yl)ethoxy)quinazolin-6-yl]-acrylamide 
• 1363358-85-3 (E)-N-[4-(3-chloro-4-fluoroanilino)-7-((7-methyl-7-azaspirocyclic[3.5]nonan-2-yl)methoxy)quinazolin-6-yl]-2-pentenamide 

Relevant articles and documents

Design, synthesis, antiproliferative activity and docking studies of quinazoline derivatives bearing oxazole or imidazole as potential EGFR inhibitors

Six series of quinazoline derivatives bearing oxazole or imidazole (8a-f, 9a-f, 10a-d, 11a-f, 12a-d and 13a-i) were designed, synthesized and their IC50 values evaluated against three cancer cell lines (A549, MCF-7 and PC-3). Most of the thirty-five target compounds showed excellent antiproliferative activity against one or several cancer cell lines. Compound 12a showed the best activity against A549, MCF-7 and PC-3 cancer cell lines, with IC50 values of 1.90 ± 0.13 μM, 2.23 ± 0.28 μM and 2.03 ± 0.14 μM, respectively. Four selected compounds (8a, 9d, 10a and 12a) were further evaluated for the inhibitory activity against EGFR kinase. AnnexinV-FITC, propidium iodide (PI) double staining and acridine orange single staining results indicated that compound 12a could induce apoptosis of human lung cancer A549 cells.

Structure-based virtual screening of Src kinase inhibitors

Src is an important target in multiple processes associated with tumor growth and development, including proliferation, neovascularization, and metastasis. In this study, hit identification was performed by virtual screening of commercial and in-house compound libraries. Docking studies for the hits were performed, and scoring functions were used to evaluate the docking results and to rank ligand-binding affinities. Subsequently, hit optimization for potent and selective candidate Src inhibitors was performed through focused library design and docking analyses. Consequently, we report that a novel compound '43' with an IC50 value of 89 nM, representing (S)-N-(4-(5-chlorobenzo[d][1,3]dioxol-4-ylamino)-7-(2-methoxyethoxy)quin azolin-6-yl)pyrrolidine-2-carboxamide, is highly selective for Src in comparison to EGFR (IC50 ratio > 80-fold) and VEGFR-2 (IC50 ratio > 110-fold). Compound 43 exerted anti-proliferative effects on Src-expressing PC3 human prostate cancer and A431 human epidermoid carcinoma cells, with calculated IC50 values of 1.52 and 0.78 μM, respectively. Moreover, compound 43 (0.1 μM) suppressed the phosphorylation of extracellular signal-regulated kinases and p90 ribosomal S6 kinase, downstream molecules of Src, in a time-dependent manner, in both PC3 and A431 cell lines. The docking structure of compound 43 with Src disclosed that the chlorobenzodioxole moiety and pyrrolidine ring of C-6 quinazoline appeared to fit tightly into the hydrophobic pocket of Src. Additionally, the pyrrolidine NH forms a hydrogen bond with the carboxyl group of Asp348. These results confirm the successful application of virtual screening studies in the lead discovery process, and suggest that our novel compound 43 can be an effective Src inhibitor candidate for further lead optimization.

Design, synthesis and biological evaluation of novel 4-anlinoquinazoline derivatives as EGFR inhibitors with the potential to inhibit the gefitinib-resistant nonsmall cell lung cancers

A series of quinazoline derivatives with benzylidene hydrazine carboxamide were designed and synthesised as EGFR inhibitors. Most compounds exhibited exceptional anti-proliferative activity against A549, HepG2, MCF-7 and H1975 cells. Furthermore, six compounds demonstrated excellent inhibition activity against EGFRWT with the IC50 value both less than 2 nM. Among the six compounds, 44 exhibited the strongest activity (0.4 nM) and potently inhibited EGFRL858R/T790M (0.1 μM). Excitingly, the most potent compound 14 showed excellent enzyme inhibitory activity with 6.3 nM and 8.4 nM for both EGFRWT and EGFRT790M/L858R. The result of AO single staining and Annexin V/PI staining showed that the compound 14 and 44 could induce remarkable apoptosis of A549 cells. The compound 14 arrested the cell cycle at the S phase and compound 44 arrested the cell cycle at the G0 phase in A549 cells. These preliminary results demonstrate that compound 14 and 44 may be promising lead compound-targeting EGFR.

A high-purity arab league law for nepal intermediate preparation method

The present invention provides a high purity arab league law for nepal preparation method of the midbody. The method comprises: the 2 - amino - 4 - fluorobenzoic acid cyclization, nitration, [...] 3, - chloro - 4 - fluoro aniline, the reaction route shown in the following chart: . The invention material price is cheap, simple operation, high purity of the product, but also easy to industrial production.