10.1021/jm901388c
The study presents the identification and development of dual PLK1/VEGF-R2 kinase inhibitors based on the 2-anilino-9-methoxy-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-ones chemotype. Researchers explored the potential of the d-annulated 1-benzazepin-2-one scaffold, found in the paullone family of kinase inhibitors, as a template for designing inhibitors that could target both PLK1 and VEGF-R2. They synthesized and tested various scaffolds, finding that those with a 9-methoxy group on the scaffold showed additional PLK1 inhibitory activity beyond their VEGFR2 inhibition. The study includes detailed synthetic methods, biological evaluations, and molecular docking studies to understand the binding modes of the compounds. The most promising compounds were found to inhibit VEGF-R2 autophosphorylation in human umbilical vein endothelial cells, sprouting of endothelial cell speroids, and proliferation of various cancer cell lines, offering a potential therapeutic approach for cancer treatment by targeting both cell division and tumor vascularization.
10.1080/00397911003629507
The research focuses on the synthesis of pyrazolo[3,4-b]- and pyrido[2,3-b]-1,5-benzodiazepines, which are heterocyclic compounds with potential pharmacological activities. The study utilizes 3-dimethylaminomethyleno-4-phenyl-1H-1,5-benzodiazepin-2-one (1) as a key intermediate, which is synthesized from 1,3-dihydro-4-phenyl-1,5-benzodiazepin-2-one and dimethylformamidedimethylacetals (DMF-DMA) in refluxing p-xylene. This intermediate is then reacted with various reagents, including hydrazines, active nitriles, and amino-heterocyclic compounds, to yield fused heterocyclic compounds 2–14. The experiments involve the use of catalysts like triethylamine and conditions such as refluxing in different solvents to facilitate the reactions. The synthesized compounds are characterized using techniques such as infrared (IR) spectroscopy, nuclear magnetic resonance (1H NMR) spectroscopy, mass spectrometry, and elemental analysis to confirm their structures and compositions.
10.1055/s-1984-31030
The research focuses on the development of a new and efficient synthesis method for monothiodiacylamines, which are valuable as reaction intermediates in the field of infectious and neoplastic diseases research. The study extends the reaction of N-acyl-N,N-dimethylamidines with nucleophiles to synthesize monothiodiacylamines, offering a more general and efficient approach compared to the four previously reported methods in the literature. The chemicals used in this process include amides, N,N-dimethylformamide dimethyl acetal, and hydrogen sulfide in acetic acid. The researchers successfully prepared N2-Acyl-N1,N'-dimethylamidines in excellent yields and then reacted them with hydrogen sulfide to obtain monothiodiacylamines in high yields (21-97%). The study concludes that their method provides a superior route for synthesizing monothiodiacylamines, which are important for further chemical transformations and pharmaceutical applications.
10.1007/BF00506592
The research investigates the reactions of 1-methylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives with acyl chlorides to synthesize 2-oxopyrimido[4,3-a]isoquinoline derivatives and 2-iminopyrimido[4,3-a]isoquinoline hydrochlorides. The study explores the properties and transformations of 1-cyanomethylene and 1-carbamidomethylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines, using reactions with benzoyl chloride, acetyl chloride, and dimethylformamide acetal to form various compounds. The key chemicals used include benzoyl chloride, acetyl chloride, dimethylformamide acetal, and phosphorus oxychloride. The research concludes that the synthesized compounds are strong bases, with ionization constants indicating significant energy gain during salt formation. The study also establishes a linear relationship between the pKa values of the synthesized compounds and the Hammett constants of their substituents, suggesting coplanarity between the benzene ring and the C=N bond in these compounds.
10.1021/jo00387a021
This research explores the cyclocondensation reactions of 3-amino-2-hydrazino-4(3H)-pyrimidinones to form 1,2,4-triazolo[4,3-a]pyrimidin-7(8H)-ones and 6H-pyrimido[1,2-b][1,2,4,5]tetrazin-6-ones. The study aims to develop a synthetic strategy for creating ring-fused systems containing nitrogen at the ring-junction, utilizing the adjacent amino and hydrazino functional groups in a heterocyclic system. The researchers reacted 3-amino-2-hydrazino-4(3H)-pyrimidinones with ortho esters, dimethylformamide dimethyl acetal, and diethoxymethyl acetate in various solvents and conditions, yielding products with substituents. Key findings include the preferential reactivity of the primary amino function of the hydrazino substituent and the isomerization of the ring-fused tetrazine derivative to a ring-fused 1,2,4-triazole.
10.1039/c1ob06690k
The study presents a novel and efficient method for synthesizing 1,4-disubstituted imidazoles with complete regioselectivity. The researchers developed a protocol that involves an unusual double aminomethylenation of a glycine derivative to yield a 2-azabuta-1,3-diene, which then undergoes transamination/cyclization with an amine nucleophile to form the substituted imidazole. Key chemicals used in the study include aminoacetonitrile, which serves as the starting material for the azadiene synthesis, and various amines as nucleophiles for the cyclization step. The study also explores the use of different reagents such as dimethylformamide dimethylacetal (DMF·DMA) and pyrrolidine to enhance the reaction efficiency and lower the reaction temperature. The method is notable for its insensitivity to steric and electronic variations on the amine component, allowing for the preparation of a diverse range of imidazoles.
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