400784-50-1

Upstream product

• 60233-66-1 5-chloroquinazolin-4-ol 
• 60233-66-1 5-chloroquinazoline-4(3H)-one 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 7463-35-6 N-(3-chloro-2-methylphenyl)acetamide 
• 19407-42-2 2-(acetylamino)-6-chlorobenzoic acid 
• 87-60-5 3-chloro-2-methylbenzenamine 

Downstream Products

• 1445768-40-0 1-(2-chloro-5-(trifluoromethyl)phenyl)-3-(3-(4-hydroxy-8-nitroquinazolin-5-ylamino)propyl)urea 
• 1445768-39-7 1-(3-(4-hydroxy-8-nitroquinazolin-5-ylamino)propyl)-3-(3-(trifluoromethyl)phenyl)urea 
• 1445768-38-6 1-(3-(4-hydroxy-8-nitroquinazolin-5-ylamino)propyl)-3-p-tolylurea 
• 1445768-37-5 1-(3-(3-hydroxy-8-nitroquinazolin-5-ylamino)propyl)-3-tolylurea 
• 1445768-36-4 4-(4-hydroxy-8-nitroquinazolin-5-yl)-N-(3-(trifluorometh-yl)phenyl)piperazine-1-carboxamide 
• 1445768-35-3 4-(4-hydroxy-8-nitroquinazolin-5-yl)-N-p-tolylpiperazine-1-carboxamide 
• 1445768-34-2 1-(2-chloro-5-(trifluoromethyl)phenyl)-3-(4-(4-hydroxy-8-nitroquinazolin-5-ylamino)cyclohexyl)urea 
• 1437304-95-4 1-(2,5-dichlorophenyl)-3-(4-(4-hydroxy-8-nitroquinazolin-5-ylamino)cyclohexyl)urea 
• 1437304-94-3 1-(4-(4-hydroxy-8-nitroquinazolin-5-ylamino)cyclohexyl)-3-p-tolylurea 
• 1437304-93-2 1-(4-(4-hydroxy-8-nitroquinazolin-5-ylamino)cyclohexyl)-3-m-tolylurea 
• 1437304-92-1 1-(2,5-dichlorophenyl)-3-(2-(4-hydroxy-8-nitroquinazolin-5-ylamino)phenyl)urea 
• 1437304-91-0 1-(2-(4-hydroxy-8-nitroquinazolin-5-ylamino)phenyl)-3-(3-(trifluoromethyl)phenyl)urea 
• 1437304-90-9 1-(3-chloro-4-methylphenyl)-3-(2-(4-hydroxy-8-nitro-quinazolin-5-ylamino)phenyl)urea 

Relevant academic research and scientific papers

3,4-Dihydroquinazolin-8-yl-3-phenylurea Derivatives: Synthesis, VEGFR-2 Kinase Inhibiting Activity, and Molecular Docking

Abstract: New 15 compounds have been synthesized targeting the highly conserved active site of VEGFR-2. Some of those have exhibited high anti-proliferation potency against tumor cells and inhibitory activity against VEGFR-2. One of the products (6h) has

Synthesis and antitumor evaluation of novel 5-substituted-4-hydroxy-8- nitroquinazolines as EGFR signaling-targeted inhibitors

The synthesis and biological activity of a series of novel 5-substituted-4-hydroxy-8-nitroquinazolines that may function as inhibitors of EGFR- and/or ErbB-2-related oncogenic signaling are described. These compounds were prepared by SNAr reaction of 5-chloro-4-hydroxy-8- nitroquinazoline with alkyl or aryl amines, or alkyl alcohol as nucleophiles. Although the enzyme assay showed a weak inhibition effect against both EGFR and ErbB-2 tyrosine kinases, the cell-based antitumor activity turned out promising. Compounds having 5-anilino substituent exhibit high potency with 5-(4-methoxy)anilino-4-hydroxy-8-nitroquinazoline (1h) being the best dual EGFR/ErbB-2 inhibitors, which effectively inhibited the growth of both EGFR (MDA-MB-468, IC50 50 = 13 μM) overexpressing human tumor cell lines in vitro. More interestingly, the variation of the substituent(s) at the 3- and/or 4-position of the 5-anilino portion was found to modulate the selectivity and potency dramatically. However, compounds having an alkylamino or alkyloxy group at the 5-position of 4-hydroxy-8-nitroquinazolines are essentially inactive. These results are consistent with molecular modeling observations. This study was the first attempt to identify new structural types of dual EGFR/ErbB-2-related signaling inhibitors by incorporation of the anilino group at the 5-position of 4-hydroxy-8-nitroquinazolines' core structure, providing promising new templates for further development of potent inhibitors targeting both EGFR and ErbB-2 tyrosine kinases.