1806-59-3Relevant academic research and scientific papers
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
Agbo, Emmanuel N.,Choong, Yee Siew,Maluleka, Marole M.,More, Garland K.,Mphahlele, Malose J.,Onwu, Eugene E.
, p. 146 - 164 (2021/12/01)
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.]
A convenient approach to 2,4-disubstituted quinazoline-3-oxides using active MnO2 as the oxidant
Ye, Xinglin,Chen, Zhiyuan,Zhang, Zhipeng,Fu, Yang,Deng, Zhihong,Peng, Yiyuan
supporting information, p. 682 - 689 (2019/09/06)
Using cheap, readily available, and economic active MnO2 as an oxidant, a series of 2,4-disubstituted quinazoline-3-oxides were synthesized in good to excellent yields by oxidation of the corresponding 1,2-dihydroquinazoline-3-oxides under mild
Rh(III)- and Zn(II)-Catalyzed Synthesis of Quinazoline N-Oxides via C-H Amidation-Cyclization of Oximes
Wang, Qiang,Wang, Fen,Yang, Xifa,Zhou, Xukai,Li, Xingwei
, p. 6144 - 6147 (2016/12/09)
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).
One-step method for synthesis of 2,4-disubstituted quinazoline 3-oxides by reaction of a 2-aminoaryl ketone with a hydroxamic acid using Zn(OTf) 2 as the catalyst
Madabhushi, Sridhar,Mallu, Kishore Kumar Reddy,Jillella, Raveendra,Kurva, Srinivas,Singh, Rajpal
supporting information, p. 1979 - 1982 (2014/04/03)
A simple and efficient method for the preparation of 2,4-disubstituted quinazoline 3-oxides by reaction of a hydroxamic acid with 2-aminoaryl ketones using zinc(II) triflate as the catalyst is described.
Intramolecular Cyclization of Iminoxyl Radicals
Atmaram, Shiravanate,Forrester, Alexander R.,Gill, Melvyn,Napier, Russell J.,Thomson, Ronald H.
, p. 641 - 648 (2007/10/02)
Iminyl radicals, generated by oxidation of the corresponding O-carboxymethoximes with persulfate, do not cyclise onto an ajacent azo group but the structurally related iminoxyls cyclise to give indazoles.ESR evidence is presented for the intramolecular ad
