10.1080/00397911.2013.807517
The research aimed to develop a simple, multicomponent, ecofriendly, and microwave-mediated route for the synthesis of antimicrobial 2-amino-6-aryl-4-(3H)-pyrimidinones. These compounds are known for their wide array of biological activities, including antimicrobial properties. The study successfully synthesized 10 such pyrimidinones in good chemical yields (44–67%), with four of them being new to the literature. The synthesized compounds were evaluated for their antimicrobial activity against Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus, with two of the compounds showing significant activity against P. aeruginosa and S. aureus, which are major pathogens in nosocomial infections. The chemicals used in the process included aromatic aldehydes, ethyl cyanoacetate, guanidine hydrochloride, and potassium carbonate, with the reactions being mediated by microwaves to accelerate the synthesis process. The study concluded that the microwave-mediated multicomponent strategy was effective in synthesizing these pyrimidinones, which have potential as broad-spectrum antimicrobial agents.
10.1016/j.tetlet.2011.11.125
The research focuses on highly efficient thermal cyclization reactions of alkylidene esters in a continuous flow reactor system, aiming to synthesize aromatic and heteroaromatic derivatives. The study was conducted at temperatures ranging from 300–360°C and under high pressure conditions (100–160 bar) with short residence times (0.45–4.5 min) in tetrahydrofuran as a solvent. The process resulted in the synthesis of substituted heteroaromatic compounds, including pyridopyrimidinones and hydroxyquinolines, as well as naphthol and biphenyl derivatives, in moderate to high yields. The continuous flow methodology offered advantages such as ease of work-up, suitability for automation, and scalability, and was considered a greener alternative due to the use of a low-boiling point solvent that can be recycled, reducing waste. The chemicals used in the process included alkylidene b-diesters, Meldrum’s acid, malonic ester, cyanoacetic acid esters, and various amines for the synthesis of the precursors and the cyclization reactions.
10.1007/s00706-011-0651-y
The study presents an efficient method for synthesizing N-arylquinoline derivatives. The key chemicals involved in this study are aromatic aldehydes, 3-arylamino-5,5-dimethylcyclohex-2-enone, and active methylene compounds such as malononitrile or ethyl cyanoacetate. These compounds undergo a one-pot multicomponent reaction catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in ethanol under microwave irradiation. The DBU acts as a catalyst to facilitate the reaction, while the microwave irradiation significantly reduces the reaction time and enhances the yield of the products. The study optimizes the reaction conditions, finding that using DBU at 5 mol% under 140 W microwave power at 80°C for 3 minutes yields the best results. This method is advantageous due to its mild reaction conditions, high product yields (92–99%), short reaction times (3–5 minutes), and compatibility with various functional groups, making it a green and efficient approach for synthesizing N-substituted quinoline derivatives, which are important in pharmaceuticals and exhibit a wide range of pharmacological activities.
10.1021/acsinfecdis.8b00279
The research aims to develop new antimalarial drugs by synthesizing and evaluating a series of pyrido[1,2-a]benzimidazole derivatives with Mannich base side chains. The study investigates these compounds' antiplasmodial activity, metabolic stability, and potential to form reactive metabolites, which can cause toxicity. Key chemicals used include ethyl acetoacetate, ethyl cyanoacetate, and various reagents for functional group transformations. The research concludes that while these derivatives show good antiplasmodial activity, they are rapidly metabolized, with less than 40% of the parent compound remaining after 30 minutes in liver microsomes. Strategies to block bioactivation were successful but at the expense of antimalarial activity. The study highlights the potential of these compounds' metabolites as future leads for drug development, given their potent activity against both chloroquine-sensitive and multidrug-resistant Plasmodium strains.
10.1016/j.cclet.2010.03.016
The study focuses on the design, synthesis, and in vitro cytotoxicity evaluation of a series of quinoline-3-carbonitrile derivatives against four cancer cell lines: A549 (lung), HT-29 (colon), MDA-MB-231 (breast), and SMMC-7721 (liver). The research aimed to develop potent and selective anti-tumor agents by replacing the quinazoline scaffold of Gefitinib, an EGFR tyrosine kinase inhibitor, with a quinoline-3-carbonitrile scaffold. The synthesized compounds were tested for their cytotoxic effects using the MTT assay, and the results showed that several of these derivatives exhibited superior selective cytotoxicity against the SMMC-7721 cell line compared to Gefitinib, with compound 11g being the most potent among them. The study also provided preliminary insights into the structure-activity relationships of these compounds, suggesting their potential as anti-cancer agents. Further research on their anti-tumor activities and detailed structure-activity relationships is ongoing.
10.1016/0040-4020(82)85032-1
The research investigates the arylation and heteroarylation of β-dicarbonyl compounds through a photostimulated SRN1 reaction. The purpose of the study is to explore new synthetic methods for heterocyclic compounds by extending the scope of the SRN1 reaction, which is known for its efficiency in arylation of monoketones but was previously thought not to occur between aryl halides and monoanions of β-dicarbonyl compounds. The researchers discovered that the presence of a cyano electron-withdrawing group allows high-yield SRN1 reactions to occur with β-dicarbonyl derived monoanions. Key chemicals used in the research include bromobenzonitriles, bromocyanopyridine, and various β-dicarbonyl compounds such as malonates, ethyl-cyanoacetate, and 2,4-pentanedione. The study concludes that the SRN1 reaction mechanism is supported by experimental observations, including the necessity of photostimulation and the influence of the cyano group's strong withdrawing effect on the reactivity. The research demonstrates that the SRN1 reaction can be efficiently applied to introduce aryl groups onto β-dicarbonyl compounds, offering a versatile and high-yield synthetic method for a variety of heterocyclic compounds.
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