K. Yu. Suponitsky

Synthesis, structure, and pharmacological activity of (7r,8s)-epoxy-(13r,17r)-trioxolane abietic acid

The synthesis of (7R,8S)-epoxy-(13R,17R)-trioxolane abietic acid was carried out and its structure was established by X-ray diffraction. The antineoplastic activity and the ability to induce apoptosis that were predicted by a PASS computer system, correlate well with the experimentally found cytotoxic activity towards the MeWo malignant cell line. The results of tests on animals showed that abietic acid and its (7R,8S)-epoxy-(13R,17R)-trioxolane derivative have anti-inflammatory and antiulcer activities in the absence of side effects.

Separation of racemic ortho-isobornylphenol into enantiomers and evaluation of their antioxidant activity

Racemic ortho-isobornylphenol was separated into enantiomers through diastereomeric camphanates. The absolute configuration of chiral centers of the isolated products was determined by X-ray studies. Antioxidant activity and membrane-protective properties of the enantiomers were studied on the model of H2O2-induced hemolysis of erythrocytes.

3-(1-Adamantyl)Furazans

The reactivity of 3-(1-adamantyl)-4-aminofurazan was studied. Upon treatment with oxidizing reagents the amino group is oxidized to azo, azoxy, and nitro groups. The nitration of 3-(1-adamantyl)-4-aminofurazan with nitric acid provided the corresponding nitroamine. The reaction of 3-(1-adamantyl)-4-nitrofurazan with nitrating and bromination agents takes place at the bridgehead position of the adamantane fragment and gives the corresponding nitroxyl and bromo derivatives. An X-ray structural analysis of 4,4′-di(1-adamantyl)azofurazan was undertaken.

Synthesis of 3-substituted 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles

A method of synthesizing new 3-substituted 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles has been developed based on the reductive cyclization of substituted 4-cyanomethyl-5-nitrophthalonitriles.

Synthesis and membrane protective activity of 4-alkoxymethyl-2,6-diisobornylphenols

Bromination of 2,6-diisobornyl-4-methylphenol gave the corresponding 4-bromomethyl derivative, whose reaction with alcohols resulted in 4-alkoxymethyl-2,6-diisobornylphenols. Their toxicity, membrane protective and antioxidant activity were tested using red blood cells of laboratory mice. The synthesized compounds do not exhibit cytotoxicity at the concentrations of 10 and 100 μmol L–1 and are characterized by high membrane protective and antioxidant activity in the concentrations of 1 and 10 μmol L–1.

Synthesis and molecular structure of di(4-hydroxy-2,6-diisoborn-2-ylphenyl)methane

Di(4-hydroxy-2-{(1R*,2S*,4S*)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}-6-{(1S*,2R*,4R*)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl})methane was synthesized by condensation of the meso-diastereomer of 2,6-diisobornylphenol with paraformaldehyde under acid catalysis. The product structure as a meso-forms was confirmed by XRD analysis.

Synthesis of new olean-18(19)-ene derivatives from allobetulin

New olean-18(19)-ene triterpenoids were effectively synthesized by the interaction of allobetulin or its acetate with phosphorous oxychloride in refluxing pyridine. The structures of the synthesized 17-chloromethyloleane-18(19)-enes were confirmed by NMR spectroscopy and X-ray analysis.

Synthesis of 4-Acyl-3-Aminofurazans from 3,4-Diacylfuroxans

It was shown that 3,4-diaroylfuroxans are transformed into the corresponding 3-amino-4-aroyl-furazans by heating in aqueous ammonia. The developed one-pot methodology for the synthesis of 3-amino-4-aroylfurazans involved the interaction of the corresponding acetophenones with nitric acid followed by treatment of the in situ formed furoxans with ammonia at elevated temperature. The structures of the obtained furazans were confirmed by IR, as well as by 1H and 13C NMR spectroscopy, and X-ray structural analysis was performed for 3-amino-4-(4-methoxybenzoyl)furazan.

Study of the interaction of imidazolidine-2-thione with molecular iodine

The crystal and molecular structure of the reaction product of imidazolidine-2-thione and molecular iodine of the composition (C3H6N2S)2•3I2 was established by X-ray diffraction. The crystal structure is composed of strongly connected five-component associates consisting of three I2 molecules and two heterocyclic molecules. Quantum chemical calculations followed by the topological analysis of the electron density function provided an estimate of the strongest intermolecular interactions in the crystal structure of the molecular adduct.

Reaction of 6-arylidene-2,2-dimethylcyclohexanones with phenylhydrazine. Molecular and crystal structures of 3-(4-halophenyl)-1-phenyl-4,5,6,7-tetrahydro-(2H)-indazoles

The previously unknown 3-(4-chlorophenyl)-7,7-dimethyl-2-phenyl-3,3a,4,5,6,7-hexahydroindazole 6a and (4-halophenyl)-7,7-dimethyl-1-phenyl-4,5,6,7-tetrahydroindazoles 7a,b were synthesized by the reaction of 6-arylidene-2,2-dimethylcyclohexanones with phenylhydrazine in the presence of pyridine. The molecular and crystal structures of compounds 7a,b were determined by X-ray diffraction.