Refernces
10.1002/aoc.3682
The research focuses on the development of a novel, green, and efficient catalytic system using zinc cation supported on λ-carrageenan magnetic nanoparticles (Zn2+/λ-carrageenan/Fe3O4) for the one-pot three-component synthesis of quinoline derivatives. The study involves the preparation of the catalyst through a series of steps, including the synthesis of nanomagnetite, coating it with λ-carrageenan, and decorating it with zinc cation. The catalyst's structure and properties were characterized using various techniques such as FT-IR spectroscopy, FE-SEM, EDX, TEM, XRD, VSM, TGA, and ICP analysis. The experiments involved a model reaction of benzaldehyde, aniline, and butanal, optimized for catalyst amount, solvent, and temperature, and then extended to a series of reactions with different substituted aldehydes and anilines. The analyses confirmed the successful synthesis of the catalyst and its high activity in the green synthesis of 16 quinoline derivatives with high yields, without the use of toxic solvents or co-catalysts.
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.
10.3184/174751912X13395258340271
The study presents a one-pot three-component synthesis method for highly substituted piperidines using 1-methyl-2-oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO4]) as an ionic liquid catalyst. The process involves aromatic aldehydes, anilines, and β-ketoesters, which are combined in refluxing ethanol to produce the piperidine derivatives. These compounds are significant due to their biological activities, including potential use in treatments for various diseases such as malaria, hypertension, bacterial infections, and diabetes. The ionic liquid catalyst offers advantages like ease of work-up, no need for column chromatography, and good to high yields, making the synthesis method efficient and environmentally friendly.
10.1055/s-0035-1561384
The study explores the development of efficient protocols for the reductive amination of ketones and aldehydes with electron-deficient anilines. The authors aimed to address the limitations of existing protocols for C–N bond formation in the context of synthesizing tool compounds for investigating phenazine biosynthesis. They established three robust and scalable methods using different reductants and activating agents: BH3·THF/AcOH/CH2Cl2 (method A), BH3·THF/TMSCl/DMF (method B), and NaBH4/TMSCl/DMF (method C). These methods demonstrated high yields and short reaction times, with method B and C being particularly efficient, achieving full conversions within 10 to 25 minutes for most substrates. The study tested these methods on a variety of substrates, including 12 anilines and 14 ketones, and defined the scope and limitations of these reactions. The findings contribute to the field of organic synthesis by providing new, efficient, and scalable protocols for reductive amination, which are particularly valuable for electron-deficient anilines.
10.1002/anie.201306511
The research focuses on the development of a traceless directing group strategy for C-H borylation reactions of nitrogen heterocycles and anilines. The main content revolves around the use of the (pinacolato)boron (Bpin) group as a traceless directing group, which can be readily installed and removed without additional steps, offering an alternative to traditional methods that require installation and removal of directing groups. The experiments involved the borylation of various substrates, including pyrroles, indoles, azaindoles, pyrazoles, and anilines, using the Bpin group. Reactants such as HBpin and iridium catalysts were used, along with tertiary amines to facilitate N-borylation. The analyses included monitoring the reactions by 1H and 11B NMR spectroscopy, and evaluating the yields and selectivity of the borylated products. The study demonstrated that the Bpin-directed approach is operationally simpler and generally higher yielding than the Boc-directed counterparts, and it expands the scope of C-H borylation by enabling functionalization at different positions on the substrates.
10.1016/j.bmc.2010.03.015
The research focuses on the synthesis and anti-HIV activity of alkylated quinoline 2,4-diols, based on naturally occurring quinolone alkaloids, buchapine and compound 2. The study aimed to evaluate their potential as anti-HIV agents in human CD4+ T cell line CEM-GFP, infected with HIV1NL4.3 virus. A series of 45 alkylated derivatives were synthesized and tested for anti-HIV potential. The key intermediates, quinoline 2,4-diol and substituted quinoline 2,4-diol, were synthesized through condensation of aniline or substituted aniline with diethyl malonate under microwave irradiation. The synthesis involved various reactants such as prenyl bromide, K2CO3, DMF, and N-methyl 2-pyrolidone (NMP). The biological evaluation included cytotoxicity testing using an MTT-based cell viability assay and anti-HIV activity determination through p24 antigen capture ELISA. The analyses used included nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared (IR) spectroscopy, high-performance liquid chromatography (HPLC), and elemental analysis to confirm the structure and purity of the synthesized compounds. The study identified several potent inhibitors, with compound 6 showing an IC50 value of 2.35 μM and a therapeutic index better than AZT, the standard anti-HIV drug.
10.1016/j.bmcl.2017.09.023
The research focuses on the discovery of highly potent and selective covalent inhibitors of JAK3, a key enzyme in the immune system. The study is based on the design of molecules that bind irreversibly to the JAK3 active site cysteine residue, utilizing crystal structure information and a comparative study of electrophilic warheads. Experiments involved the synthesis of compounds, such as 9a and 9b, and their evaluation for JAK3 inhibition through enzymatic assays, cellular assays, and kinome selectivity screens. Reactants used in the synthesis included intermediates like meta-nitro benzylamine and aniline, which were subjected to hydrogenolysis and acylation to produce the final compounds. The analyses used to assess the compounds' potency and selectivity included fixed time point enzymatic assays, cellular potency assays, and broad kinome selectivity screens against over 350 kinases. The results indicated that 9a was a highly potent JAK3 inhibitor with excellent selectivity, while further exploration of alternative electrophilic groups in the pyrazolopyridazine series led to the identification of 13a, which confirmed covalent interaction with Cys909 in the JAK3 active site through X-ray crystallography and kinetic evaluation.
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