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Vol 59, No 2 (2023)
Articles
Synthesis of 4-(N4-methyl-5-aryl-1,2,4-triazole-5-ilmethylthio) cresoxyacetic acids and their sulfonic analogues of new potential PPARδ/β agonists
Abstract
A nine-stage scheme for the synthesis of 4-( N 4-methyl-5-aryl-1,2,4-triazole-5-ilmethylthio) cresoxyacetic acids of new potential PPARδ/β agonists based on substituted benzoic acids has been developed. Their sulfon-containing analogues were obtained from the intermediate esters of such acids.
Žurnal organičeskoj himii. 2023;59(2):145-164
145-164
Synthesis and affinity of novel asialoglycoprotein receptor triantennary ligands
Abstract
New triantennary N -acetylgalactosamine derivatives of tris(hydroxymethyl)aminomethane were synthesized and used to form complexes with asialoglicoprotein receptor, originally found on hepatocytes. Equilibrium dissociation constants ( K D) of asialoglicoprotein receptor and obtained compounds were measured using surface plasmon resonance spectroscopy technique. The K D values were in the subnanomolar range, being 6 orders of magnitude lower than the K D of the complex of the receptor and N -acetylgalactosamine, its native ligand. The synthesized ligands exhibit much stronger binding to receptor in comparison to the natural ligand. These results suggest that synthesized ligands are promising agents for the targeted delivery of various therapeutic agents in hepatocytes.
Žurnal organičeskoj himii. 2023;59(2):165-179
165-179
Synthesis of spiro(pyrrol-2,5'-pyrrolo[2,3-d]pyrimidine)2',4',5,6'-tetraones by the reaction of pyrrolo[2,1-c][1,4]oxazinetriones with 6-aminopyrimidine-2,4-diones
Abstract
8-Aroyl-3,4-dihydro-1 H -pyrrolo[2,1- c ][1,4]oxazine-1,6,7-triones react with 6-aminopyrimidine-2,4(1 H ,3 H )diones to form 3-aroyl-4-hydroxy-1-(2-hydroxyalkyl)spiro(pyrrole-2,5'-pyrrolo[2,3- d ]pyrimidine)2',4',5,6'(1 H ,1' H ,3' H ,7' H )-tetraones, the structure of which was confirmed by X-ray diffraction analysis.
Žurnal organičeskoj himii. 2023;59(2):180-186
180-186
Push-pull systems based on 2,4,6-triaryl pyrimidines. 2,4-diaryl-6- and 2-aryl-4,6-bis{4-[(E)-2-arylvinyl]phenyl}pyrimidines
Abstract
Previously undescribed 2,4,6-triarylpyrimidines were synthesized by condensation of benzamidine and 4-(methyl-, 4-butoxy)benzamidine hydrochlorides with ( E )-1,3-diaryl-2-propen-1-ones in alcohol in the presence of KOH. The latter were reacted with ( E )- N -(2-chlorophenyl)-1-arylmethanimines in the KOH/LiH/DMF system to give 2,4-diaryl-6- and 2-aryl-4,6-bis{4-[( E )-2-arylvinyl]phenyl}-pyrimidines.
Žurnal organičeskoj himii. 2023;59(2):187-196
187-196
Multicomponent synthesis of functionalized 2-amino-4H-pyrans initiated by the Knoevenagel reaction
Abstract
The multicomponent condensation of aldehydes, malononitrile derivatives, 1,3-dicarbonyl compounds of the carbo- and heterocyclic series, and alkyl halides has been studied. The transformation is initiated by the Knoevenagel reaction and leads to the formation of functionally substituted condensed 2-amino- 4 H-pyrans. The structure of a number of products was studied by X-ray diffraction.
Žurnal organičeskoj himii. 2023;59(2):197-210
197-210
Reaction mechanism of the formation of N-methyl-N-[2-(diphenylphosphoryl)-ethyl]amide of diphenylphosphorylacetic acid
Abstract
The reaction mechanism of the formation of N -methyl-substituted diphenylphosphorylacetic acid amide was studied by DFT. According to theoretical calculations, at the first stage, explicit allowance for the solvent makes it possible to reduce the activation energy of three elementary stages of the interaction of trichlorophosphine with diphenylphosphorylacetic acid; at the second stage, the interaction of diphenylphosphorylacetic acid chloride with a phosphoryl-containing amine proceeds in one elementary stage.
Žurnal organičeskoj himii. 2023;59(2):211-216
211-216
Synthesis and inhibitory activity of atorvastatin conjugate with a branched asialoglycoprotein receptor ligand with 3 N-acetyl-d-galactosamine residues
Abstract
The novel atorvastatin conjugate was synthesized in a multi-step procedure using branched N -acetylgalactosamine ligand for asialoglycoprotein receptor targeting. The molar solubility of the obtained conjugate was 6.1±0.9 mM, which is almost 60 times higher than that of unmodified atorvastatin. The hydrolysis products of the conjugate demonstrated effective inhibition of 3-hydroxy-3-methyl-glutaryl-coenzyme A reductase.
Žurnal organičeskoj himii. 2023;59(2):217-227
217-227
The first example of synthesis of a new class of spiroboracarbocycles via cycloboration of methylenecycloalkanes with PhBCl2 catalyzed by Cp2TiCl2
Abstract
Cp2TiCl2-catalyzed cycloboration of methylenecycloalkanes with PhBCl2 in the presence of metallic Mg to obtain a novel spiroboracarbocycles in good yields (70-80%) is reported for the first time. The structure and properties of spiro-fused boriranes were studied using 11B, 1H, 13C NMR spectroscopy and DOSY experiments. 1-Phenyl-substituted boraspiranes are stable in solution at room temperature for a day.
Žurnal organičeskoj himii. 2023;59(2):228-236
228-236
Synthesis of C60 fullerene hybrid molecules with catecholamines under the action of ultrasound
Abstract
For the first time, morpholine monoadducts of С60-fullerene were obtained in the reactions of fullerene with biogenic amines (norepinephrine, adrenaline) under the action of ultrasound. The reactions take place in air in ( g 2.0000 and Δ H 1/2 3.2 G) was detected by EPR, a key intermediate in the synthesis of the C60-adrenaline cycloadduct, which was obtained as a result •-a toluene/DMF medium at room temperature. The radical anion C60- of a one-electron transition from the adrenaline molecule to the C60 framework.
Žurnal organičeskoj himii. 2023;59(2):237-242
237-242
Synthesis of new macrocyclic triperoxides
Abstract
An efficient method has been developed for the synthesis of dialkyl hexaoxadispiroalkanedicarboxylates by the recyclization reaction of heptaoxadispiroalkanes with alkyl malonates (malonic acid dimethyl ester, malonic acid diethyl ester, malonic acid diisopropyl ester) under the action of lanthanide catalysts.
Žurnal organičeskoj himii. 2023;59(2):243-249
243-249
Catalytic cross-cyclomagnesiation reaction in the synthesis of 4Z-unsaturated iodo-δ-lactones
Abstract
A three-stage synthesis of 4 Z -unsaturated iodo-δ-lactones based on 5 Z ,9 Z -dienic acids was carried out using the intermolecular cross-cyclomagnesiation reaction of aliphatic and O-containing 1,2-dienes catalyzed by Cp2TiCl2 at the key stage with yields of 92-96% and selectivity 98-99%.
Žurnal organičeskoj himii. 2023;59(2):250-255
250-255
Mannich reaction in the synthesis of azaperoxides
Abstract
The applicability of the Mannich reaction in the synthesis of new tetraoxazodispiroalkanes by a three-component reaction of primary arylamines with gem-dihydroperoxides and cyclohexanone with the participation of Sm(NO3)3 6H2O as a catalyst has been established.
Žurnal organičeskoj himii. 2023;59(2):256-260
256-260
261-265
266-270
271-276