808762-36-9

Upstream product

• 948551-62-0 C₁₁H₁₁ClN₂O₃ 
• 62-53-3 aniline 
• 20323-74-4 2-carboethoxy-4,5-dimethoxyaniline 
• 100905-33-7 ethyl 2-nitro-4,5-dimethoxybenzoate 
• 3943-77-9 ethyl veratrate 
• 93-07-2 Veratric acid 
• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 

Downstream Products

• 808762-37-0 7-methoxy-4-(phenylamino)quinazolin-6-ol 

Relevant academic research and scientific papers

Synthesis, Biological Activity, and Crystal Structure of N,N-Diethyl-2-{[7-methoxy-4-(phenylamino)quinazolin-6-yl]oxy}acetamide Derivatives

Abstract: A number of novel 4-aminoquinazoline derivatives has been synthesized by four-step synthesis. Structures of the synthesized compounds have been characterized by IR and 1H NMR spectra, element analysis, and single crystal X-ray diffraction. Biological activity of the products has been tested and most of those are characterized by potential antitumor activity against MKN45 cell line. Two compounds exhibit significant inhibitory activity higher than that of Gefitinib used as the positive control. Preliminary structure-activity relationship is considered.

Design, synthesis and biological evaluation of sulfamoylphenyl-quinazoline derivatives as potential EGFR/CAIX dual inhibitors

Multi-target, especially dual-target, drug design has become a popular research field for cancer treatment. Development of small molecule dual-target inhibitors through hybridization strategy can provide highly potent and selective anticancer agents. In this study, three series of quinazoline derivatives bearing a benzene-sulfonamide moiety were designed and synthesized as dual EGFR/CAIX inhibitors. All the synthesized compounds were evaluated against epidermoid carcinoma (A431) and non-small cell lung cancer (A549 and H1975) cell lines, which displayed weak to potent anticancer activity. In particular, compound 8v emerged as the most potent derivative against mutant-type H1975 cells, which exhibited comparable activity to osimertinib. Importantly, 8v exhibited stronger anti-proliferative activity than osimertinib against H1975 cells under hypoxic condition. Kinase inhibition studies indicated that 8v showed excellent inhibitory effect on EGFRT790M enzyme, which was 41 times more effective than gefitinib and almost equal to osimertinib. Mechanism studies revealed that 8v exhibited remarkable CAIX inhibitory effect comparable to acetazolamide and significantly inhibited the expression of p-EGFR as well as its downstream p-AKT and p-ERK in H1975 cells. Notably, 8v was found to inhibit the expression of CAIX and its upstream HIF-1α in H1975 cells under hypoxic condition. Molecular docking was also performed to gain insights into the ligand-binding interactions of 8v inside EGFRWT, EGFRT790M and CAIX binding sites.

Synthesis, crystal structure and anticancer activity of substituted quinazoline derivatives

News series of substituted quinazoline derivatives has been synthesized from 3,4-dihydro-7-methoxy-4-oxoquinazoline-6-yl acetate (1) by five-step procedures including chlorination, amination, hydrolysis and etherification. The structures of target compounds were confirmed by IR, 1H-NMR, element analysis and single-crystal X-ray diffraction. The results showed that the compound 8c exhibited remarkable inhibitory activity against MCF-7 cell lines with inhibition rate value of 38.45 %, which was comparable to that of the positive control Gefitinib (inhibition rate = 13.25 % for MCF-7). The initial relationship between structure and activity was worth further exploration.

Facile Synthesis of Novel Perfluorocarbon-Modulated 4-Anilinoquinazoline Analogues

4-Anilinoquinazoline analogues stand out among many kinds of small molecules that inhibit the tyrosine kinase activities of epidermal growth factor receptor (EGFR), thus serving as significant molecular targets for anticancer drug design. Herein, a series of novel perfluorocarbon (PFC) modulated 4-anilinoquinazolines were designed and prepared straightforwardly by nucleophilic substitution reaction of various anilinoquinazolines and PFC-derived methanesulfonate. In the presence of base, the reaction proceeded smoothly to afford a wide range of 4-anilinoquinazolines with different substituents on aniline moiety in good to high yields. Furthermore, the PFC-modified analogues of gefitinib and erlotinib were also obtained in 93% and 90% respectively, which may have potential for developing new inhibitors of the epidermal growth factor receptor (EGFR) tyrosine kinase and fluorinated contrast agents (CA) for 19F MRI.

Phenalene derivatives

Novel 1,3,4-triaza-phenalene and 1,3,4,6-tetraazaphenalene derivatives are disclosed. These compounds inhibit epidermal growth factor receptor (“EGFR”) tyrosine kinase. These compounds and their pharmaceutically acceptable salts and esters have antiproliferative activity and are useful, inter alia, in the treatment or control of cancer, in particular solid tumors. This invention also relates to pharmaceutical compositions containing such compounds and to methods of treating or controlling cancer, most particularly the treatment or control of breast, lung, colon and prostate tumors.