10.1016/j.ejmech.2021.113609
The research focuses on the design, synthesis, and evaluation of new quinazolin-4-one derivatives as potential anticancer agents, specifically targeting their ability to enhance apoptosis and inhibit autophagy in tumor cells. The study experimentally investigates these compounds' cytotoxic activity against MCF-7 (breast cancer) and A-549 (lung cancer) cell lines, with compound 17 emerging as the most potent. The experiments involved the synthesis of a series of quinazolin-4-one derivatives using various reactants such as 2-aminobenzoic acid, bromine, acetic anhydride, and different substituted chloroacetanilides, among others. The synthesized compounds were characterized using techniques like IR spectroscopy, NMR spectroscopy, elemental analysis, and mass spectrometry. The biological evaluation included SRB assay for cytotoxicity, annexin V/PI staining for apoptosis, cell cycle analysis, real-time polymerase chain reaction (RT-PCR) for gene expression analysis, in vivo testing in a mouse model of breast cancer, and molecular docking studies to predict the binding mode of the compounds to the epidermal growth factor receptor (EGFR). These experiments collectively aimed to assess the anticancer potential of the synthesized quinazolin-4-one derivatives, their mechanism of action, and their interaction with EGFR, a key target in cancer therapy.
10.1016/j.molstruc.2010.05.038
The study presents a density functional theory (DFT) and experimental investigation of N,N'-bis(3-carboxy,4'-aminophenyl)-1,4-quinonediimine, a carboxyl-substituted aniline trimer. The research aims to understand the electronic and steric effects in co-polymers of aniline and anthranilic acid, and to explore the trimer's potential in corrosion inhibition. Chemicals used include 1,4-phenylenediamine, hydrochloric acid, ammonium persulfate, anthranilic acid, and ammonium hydroxide for the synthesis of the trimer. The synthesized trimer was then subjected to various experimental analyses, including UV-vis, near-IR, and NMR spectroscopy, to study its properties. The study also utilized computational methods to optimize the structures of the trimer's isomers and calculate their electronic properties, providing insights into the trimer's behavior in different oxidation states and solvent environments. The purpose of these chemicals was to synthesize the trimer and understand its redox properties, its ability to 'self-dope', and its effectiveness in corrosion inhibition, particularly in alkaline environments where standard oligo- and polyanilines fail.
10.1016/j.tetlet.2006.04.096
This research article details the one-pot synthesis of quinazolinone derivatives, which are important fused heterocycles with a range of biological activities such as anti-cancer, anti-inflammatory, and anti-malarial properties. The study aimed to develop an efficient method for the synthesis of 4(3H)-quinazolinones using anthranilic acid, trialkyl orthoformate, and amines in the presence of catalysts lanthanum(III) nitrate hexahydrate [La(NO3)3·6H2O] or p-toluenesulfonic acid (PTSA) under solvent-free conditions. The process was found to be simple, efficient, and environmentally friendly, yielding 4(3H)-quinazolinones in a single step with mild catalysts, fast reaction times (5–15 minutes), and excellent yields (82–98%). The chemicals used in the process include anthranilic acid, various substituted alkyl and aryl amines, trimethyl or triethyl orthoformate, and the catalysts La(NO3)3·6H2O or PTSA. The conclusions highlight the advantages of the protocol, such as the solvent-free conditions, simplicity of the experimental procedure, and the high yields obtained, making it a practical alternative to previous methods with environmental and economic considerations.
10.1002/ardp.19763090105
This study discusses the synthesis and investigation of 1,3-dicarbonyl compounds with a particular focus on cyclized quinolones. The aim of this study was to obtain quinolone lb via thermal condensation of 3-benzofuranone and anthranilic acid and to report the synthesis of substituted 2-benzoyl-3-hydroxy-benzo[b]thiophenes that can cyclize to form cyclized quinolones 7. This study aimed to explore the potential of heterocyclic ketones in the formation of cyclized quinolones, with oxygen, nitrogen, or sulfur as heteroatoms instead of methylene groups. The key chemicals used in the process included 3-benzofuranone, anthranilic acid, N-methylanthranilic acid, 3-acetoxyindole, thioindoxyl, and various heterocyclic compounds. The conclusions drawn from the study indicated that the cyclization was mainly carried out via Schiff bases and that the synthesis of indoles and benzothieno[3,2-b]-quinolones could be similar to the synthesis of cyclized chromones from heterocyclic β-dicarbonyl compounds. The study also highlights the potential pharmaceutical value of benzothieno[3,2-b][1]-chromones and benzothieno[3,2-b][1]-chromone-derived substances due to their antiallergic and antiallergic effects, as well as the discovery of O-ketoimidates and O-ketoamidines as new anti-inflammatory agents with no ulcerogenic effects on the gastrointestinal mucosa.
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