Synonyms:ammonium cerium(4+) nitrate (2:1:6)
98%,99%, *data from raw suppliers
The research focuses on the copper-catalyzed synthesis of trinuclear N-fused hybrid scaffolds using cyclic ureas as new building blocks. The main experiment involves the coupling and cyclization of 2-(2-bromoaryl) and 2-(2-bromovinyl)-benzimidazoles with cyclic ureas in the presence of a copper catalyst and a base, specifically potassium carbonate (K2CO3), in dimethylformamide (DMF) at 130°C for 12 hours. This process yields trinuclear N-fused hybrid scaffolds, such as benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazolines, in good yields. The study also explores the oxidation of methoxy-substituted scaffolds to form unprecedented benzimidazolequinone-fused hybrid scaffolds using ceric ammonium nitrate (CAN) in acetonitrile/H2O. The analyses used to characterize the synthesized compounds include 1H and 13C NMR spectroscopy, high-resolution mass spectrometry (HRMS), infrared (IR) spectroscopy, and melting point determination.
The research focuses on the development of a novel acetalization method for ketones and aldehydes under non-acidic conditions, utilizing diazophenanthrenequinone and PdBr2 as catalysts. The purpose of this method is to protect carbonyl groups from unwanted side reactions during multistep organic synthesis, by converting them into acetals that incorporate a phenanthrene skeleton. These newly formed acetals are stable under mild acidic conditions and can be selectively removed under strong acidic or oxidation conditions using aqueous ceric ammonium nitrate (CAN), reverting back to the original carbonyl compounds. The study concludes that this PdBr2-catalyzed acetal formation reaction is an effective and selective approach for protecting and deprotecting carbonyl groups, with potential applications in the synthesis of complex and functional organic compounds.
This study focused on the synthesis of nitrophenols and their cytotoxicity against various cancer cell lines by oxidation of phenol derivatives using cerium ammonium nitrate (CAN) in acetonitrile under mild conditions. This study aimed to elucidate the reaction conditions of CAN in the cyclonitration and oxidative addition of phenol derivatives and explore the structure-activity relationship of the resulting compounds. The researchers found that CAN is an efficient nitrating agent for phenols and tolerates a variety of functional groups such as -CH3, -I, and -CO2H under the reaction conditions. In the case of methylphenol and hydroxycarboxylic acid, steric effects were observed to reduce the nitration reaction. Cytotoxicity evaluation revealed that some compounds such as 2c, 3a, 4b, and 10b exhibited selective activity against specific cancer cell lines, with compound 10b showing cytotoxicity against Hep G2, Hep 3B, MCF-7, and MDA-MB-231 cancer cell lines. The study concluded that the p-nitrophenol functionality and p-quinone moiety in these compounds play an important role in their cytotoxic effects.
The research aimed to synthesize 4-cyanophenyl 2-azido-2-deoxy- and 3-azido-3-deoxy-1,5-dithio-β-D-xylopyranosides, which are carbohydrate derivatives with potential antithrombotic activity. The study built upon previous work by modifying the structure of beciparcil, a known antithrombotic agent, by replacing hydroxyl groups with azido groups to enhance its oral activity. Key chemicals used in the synthesis process included 3,4-di-O-benzoyl-1,5-anhydro-5-thio-D-threo-pent-1-enitol, sodium azide, ceric ammonium nitrate, trimethylsilyl triflate, and 4-cyanothiophenol, among others. The synthesized compounds were then tested for their oral antithrombotic activity in rats, with results showing that the introduction of azido groups significantly increased the activity compared to the parent compound beciparcil. However, the activity decreased upon acetylation of the amino group in the synthesized derivatives. The study concluded that compounds 3, 4, and 36 possess high oral antithrombotic activity, with the α-anomer 34 being inactive.
The research focuses on the design and synthesis of novel quinone inhibitors targeting the redox function of the multifunctional enzyme apurinic/apyrimidinic endonuclease 1/redox enhancing factor 1 (Ape1/Ref-1), which plays a crucial role in DNA repair and transcription regulation. The study involved synthesizing a series of benzoquinone and naphthoquinone analogues, particularly based on the known inhibitor E3330, to evaluate their inhibitory effects on Ape1's redox activity and tumor cell growth. Key reactants included various substituted phenols and phosphonates, with reactions facilitated by methods such as Emmons condensation and oxidation using reagents like nitric acid and ceric ammonium nitrate. Analyses included electrophoretic mobility shift assays (EMSA) to measure redox inhibition and MTS assays to assess cell growth inhibition, providing insights into structure-activity relationships and the potential therapeutic applications of these compounds.
The study focuses on the synthesis of isotopically labeled pyrroloquinoline quinone (PQQ), a cofactor found in various microbial dehydrogenases, oxidases, and mammalian copper-containing amine oxidases. The researchers adopted and modified existing chemical synthesis schemes to prepare different isotopically labeled PQQ derivatives, such as 3-13C-PQQ, 3-2H-PQQ, and 8-2H-PQQ. The synthesis of 3-13C-PQQ and 3-2H-PQQ involved the Japp-Klingemann hydrazone synthesis, Fischer indolixation, and Doebner-Von Miller type condensation, using starting materials like methoxy-nitro-aniline and methyl-acetoacetate. For 8-2H-PQQ, a Pfitzinger quinoline synthesis was employed, starting from aminoindole and using reagents like isatin, pyruvic acid, and ceric ammonium nitrate. These isotopically labeled PQQ compounds are valuable for studying the biosynthesis, enzymatic redox catalysis, and physiological role of PQQ in different organisms.
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