1837-71-4Relevant articles and documents
Behavioural response of Triatoma infestans (Klug) (Hemiptera: Reduviidae) to quinazolines
Alzogaray,Fontan,Camps,Masuh,Santo Orihuela,Fernandez,Cork,Zerba
, p. 1190 - 1196 (2005)
The behavioural responses of the haematophagous bug Triatoma infestans towards some previously identified components of its faeces: 4-methylquinazoline, 2,4-dimethylquinazoline and their mixtures were evaluated using a video tracking system. Fifth instar nymphs and females but not males were significantly attracted to polyethylene glycol formulations of 4-methyl + 2,4-dimethylquinazoline (50 [μg each). Fifth instar nymphs were also attracted to 4-methylquinazoline alone (50 μg) but females were only attracted by the mixture of both methyl quinazolines (50 μg each). Syntheses of both methyl quinazolines were carried out starting from 2-aminoacetophenone by modifying the conditions of reported procedures.
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.]
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
supporting information, 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.
