Refernces
10.1016/j.ejmech.2009.12.021
The research focuses on the hydrogenative desulphurization of thienopyrrolizinones, aiming to dearomatize tripentones with potential antineoplastic activities. The study unexpectedly led to the formation of (Z)-phenethylidenepyrrolizinones, which were then tested for in vitro cytotoxic activity against the human epidermoid carcinoma KB cell line. The experiments involved the use of various catalysts such as palladium, rhodium, and platinum on charcoal, as well as Raney Nickel, under atmospheric pressure to achieve the reduction of heterocyclic isosters. The synthesized compounds were characterized using techniques like infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). The biological evaluation of the compounds was conducted by treating KB cells with various concentrations of the compounds, and the inhibition of cell proliferation was measured using the MTS assay. The results indicated that the tricyclic core of the model could be modified while maintaining some level of cytotoxic activity.
10.1016/S0960-894X(02)01064-8
The study focuses on the synthesis, antiviral activity, and pharmacokinetics of P1/P10 substituted 3-aminoindazole cyclic urea HIV protease inhibitors. The aim was to enhance the intracellular antiviral potency of nonsymmetrical 3-aminoindazoles, DMP 850 and DMP 851, by modifying the P1/P10 residues to improve cell penetration. The chemicals used included various substituted benzyllithiums, dihydrazone 1, Raney nickel, and 1,10-carbonyldiimidazole for synthesis; 3-cyano4-fluoro-benzylbromide and hydrazine hydrate for introducing the 3-aminoindazole group; and benzyl bromide or butyl iodide for alkylation to form mono-alkylated cyclic ureas. These chemicals served to create a series of P1/P10 substituted cyclic urea analogues, which were then tested for their enzyme binding affinity, whole cell antiviral activity, plasma protein binding, resistance profile, and pharmacokinetics to assess their potential as therapeutics for inhibiting the human immunodeficiency virus protease (HIV-Pr).
10.1055/s-1987-28081
The research focuses on the development of a novel method for furan annelation through the regioselective acylation of allylic sulfides via α-silyl intermediates. The purpose of this study was to provide a facile entry to furan derivatives, which are important in organic synthesis, by utilizing acid-catalyzed acylation and subsequent acid-catalyzed cyclization. The researchers successfully synthesized a series of α-phenylthiofuran derivatives and furan derivatives with good yields. Key chemicals used in the process include allylic sulfides, acid chlorides, aluminum chloride as a catalyst, concentrated sulfuric acid for cyclization, Raney nickel for reductive desulfurization, and various solvents such as dichloromethane, benzene, and ether.
10.1021/jacs.0c13077
The research focuses on the development of a novel and sustainable method for multicomponent dicarbofunctionalization (DCF) of alkenes through photochemical C?H activation, utilizing nickel-catalyzed olefin dicarbofunctionalization. The purpose of this study was to overcome the limitations of using prefunctionalized radical precursors in multicomponent reactions, which typically exhibit poor atom economy, by activating native C?H bonds for the construction of complex small molecules. The researchers discovered that diaryl ketones, acting as hydrogen-atom transfer (HAT) catalysts, in conjunction with nickel catalysts, could effectively activate C?H bonds, leading to the formation of new carbon?carbon bonds.
10.1021/jo101910r
The study presents a nine-step total synthesis of the quinolizidine alkaloid (+)-Epilupinine with an overall yield of 48%. The key step in this synthesis is the intramolecular nitrile oxide-alkene cycloaddition (INOC), which is used to construct the quinolizidine skeleton. The researchers developed a novel method to efficiently prepare the challenging intermediate (R)-(2-vinylpiperid-1-yl)propanal oxime (13a) from (R)-(2-vinylpiperid-1-yl)propanol (11a) using a two-step process involving Mitsunobu reaction and N-detosylation, avoiding the use of the highly unstable aldehyde intermediate. This method was further generalized to convert various 3-(N,N-dialkylamino)propanols into their corresponding oximes. The final steps of the synthesis involve a Raney nickel-promoted desulfurization to yield the target compound (+)-Epilupinine. The study not only provides a practical and scalable route to this biologically important alkaloid but also offers a new approach for the application of INOC in the total synthesis of other alkaloids.
10.1248/cpb.34.1917
The research focused on the synthesis and conformational analysis of 1-Methyl-3,4-benzo-7-thia-2-azabicyclo[3.3.1]nonane 7-oxide, a novel tricyclic compound with potential antispasmodic activity. The compound was synthesized through the reaction of quinaldine with methylsulfinylmethyl carbanion, and its structure was elucidated using spectral data and chemical evidence. The conformational analysis was conducted using proton and carbon-13 nuclear magnetic resonance spectroscopy, along with molecular mechanics calculations, which indicated that the stable conformer has a chairthiane ring with an equatorial sulfoxy group. Key chemicals used in the process included quinaldine, methylsulfinylmethyl carbanion, dimethylsulfoxide (DMSO), Raney nickel for desulfurization, and various quinaldine derivatives. The research concluded that the synthesized compound and its derivatives adopt a chair conformation with an equatorial sulfoxy group, which was consistent with the observed NMR data and molecular mechanics calculations.
10.1021/jm00272a031
The research focuses on the synthesis and characterization of new chemical compounds with potential applications in medicinal chemistry. The primary purpose of the study is to develop and analyze novel compounds that may have therapeutic properties or serve as intermediates in the production of pharmaceuticals. The researchers synthesized compounds such as 2-fluoro-9-(p-D-ribofuranosyl)purine (2a) and 9-(2,3,5-tri-O-acetyl-α-D-ribofuranosyl)-2-fluoropurine (2b), using various chemical reagents and techniques. Key chemicals involved in the synthesis include Raney nickel, ethanol, hydrofluoric acid, sodium nitrite, and acetic anhydride, among others. The conclusions drawn from the study highlight the successful synthesis of the target compounds and their structural confirmation through analytical techniques. The research contributes to the field of medicinal chemistry by providing new compounds that can be further explored for their biological activities and potential applications in drug development.
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