1643-59-0

Basic information

• Product Name: 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide
• Synonyms: 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide
• CAS NO: 1643-59-0
• Molecular Weight: 270.718
• Mol File: 1643-59-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide(1643-59-0)
• EPA Substance Registry System: 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide(1643-59-0)

Safety Data

• Hazardous Substances Data: 1643-59-0(Hazardous Substances Data)

Upstream product

• 1640-44-4 N-(2-acetyl-phenyl)-4-chloro-benzamide 
• 4964-49-2 1-(2-aminophenyl)ethanone oxime 
• 551-93-9 2-aminoacetophenone 
• 1613-88-3 4-chloro-N-hydroxybenzamide 
• 613-91-2 acetophenone oxime 
• 132401-91-3 3-(4-chlorophenyl)-1,4,2-dioxazol-5-one 

Relevant articles and documents

Synthesis, in vitro and in silico enzyme (COX-1/2 & LOX-5), free radical scavenging and cytotoxicity profiling of the 2,4-dicarbo substituted quinazoline 3-oxides

Series of the 3-methylquinazoline 3-oxide derivatives were evaluated through enzymatic assays in vitro and in silico for potential inhibitory effect against cyclooxygenase-1/2 (COX-1/2) and lipoxygenase-5 activities as well as for free radical scavenging potential and cytotoxicity. The 6-bromo (3k) and 6-iodo substituted 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide (3q) exhibited significant inhibitory effect against both COX-1 (IC50 = 13.9 ± 3.21 μM and 9.7 ± 0.09 μM, respectively) and COX-2 (IC50 = 6.4 ± 0.74 μM and 4.6 ± 1.45 μM, respectively) compared to quercetin (IC50 = 13.84 ± 1.57 μM and 5.06 ± 2.60 μM, respectively). Their activity was, however, modest compared to the selective COX-2 inhibitor, celecoxib, with IC50 values of 7.35 ± 0.88 μM and 0.62 ± 0.74 μM against COX-1 and COX-2, respectively. The two compounds exhibited comparable effect on LOX-5 (IC50 = 15.0 μM), which is moderate compared to quercetin (IC50 = 8.04 ± 1.12 μM) and modest against zileuton (IC50 = 0.42 ± 0.51 μM). Structure–activity relationship analysis suggested that the presence of a halogen atom at the C-6 position and a 2-aryl group enhance inhibitory effect against COX-2. This observation is well supported by molecular docking studies. [Figure not available: see fulltext.]

Rh(III)- and Zn(II)-Catalyzed Synthesis of Quinazoline N-Oxides via C-H Amidation-Cyclization of Oximes

Quinazoline N-oxides have been prepared from simple ketoximes and 1,4,2-dioxazol-5-ones via Rh(III)-catalyzed C-H activation-amidation of the ketoximes and subsequent Zn(II)-catalyzed cyclization. The substrate scope and functional group compatibility were examined. The reaction features relay catalysis by Rh(III) and Zn(II).