Vol 59, No 5 (2023)

As a result of the reaction of 5-substituted 4-trichloroacetylfuran-2,3-diones with aromatic amines, 4-substituted 5-hydroxy 5-(trichloromethyl)dihydrofuran-2,3-diones, were synthesized, which have antibacterial and antinociceptive activities.

The interaction of halogen-substituted benzaldehydes with 3-(1-chloroethoxy)prop-1-yne leads to the formation of unsaturated ethers of 2-hydroxyoxirane. The formation of the latter was confirmed by the reaction of the latter with acetone in the presence of BF₃·Et₂O with the formation of substituted 1,3-dioxolanes.

The mass spectra of previously unknown N -(5-amino-2-thienyl)thioureas obtained in one preparative step from propargylamines and isothiocyanates were studied for the first time, and the main patterns of their fragmentation under electron ionization conditions (70 eV) were revealed. All thienylthioureas studied form a molecular ion ( I _rel 7-61%), whose general direction of fragmentation {with the exception of N -[5-(diethylamino)-2-thienyl]- N , N '-diphenylthiourea} is the breaking of the R¹N-C(=S) bond with the formation of the [ M - R²NHCS]⁺ ion, the peak of which has a high intensity ( I _rel 35-85%). The dominant direction of fragmentation of the molecular ion N -[5-(diethylamino)-2-thienyl]- N , N '-diphenylthiourea is associated with the degradation of the thiophene cycle by C₂-S and C₄-C₅ bonds. For N -(5-pyrrolidine-1-yl-2-thienyl)- and N -(5-piperidine-1yl-2-thienyl)thioureas are characterized by the course of intensive specific rearrangement processes, manifested in the appearance of unexpected channels of primary fragmentation of the molecular ion, the main of which is the elimination of the molecule N , N '-dimethylcarbodiimide.

Eight new N -acylhydrazones were synthesized from betulin diacetate by its low-temperature ozonolysis to obtain 3β,3,28-diacetoxyoxy-20-oxo-29-norlupan and condensation of the latter with hydrazides of aliphatic and aromatic acids. Cytotoxic activity of the obtained compounds in relation to a number of tumor cells was studied in vitro . Derivatives obtained by condensation of 3β,3,28-diacetoxy-20-oxo-29-norlupan with hydrazides of salicylic, isonicotinic and nicotinic acids showed moderate activity against cell lines of human hepatocellular carcinoma HepG2, human colon cancer HTC-116, leukemia THP-1, acute T-cell leukemia Jurkat.

By interaction between few recently prepared 2,5,7-substituted 6-keto(hydroxy)-1,3-diazaadamantanes and anhydrides of different dicarbonic acids 15 new diazaadamantane analoques, containing phthalimide or succinimide fragments have been prepared.Target compounds were tested for antibacterial activity.

The interaction of 2-[3(4)-nitrobenzoyl]-1,1,3,3-tetracyanopropenides with hydrogen chloride in alcohols leads to the corresponding 4-amino-1-alkoxy-1-[3(4)-nitrophenyl]-3-oxo-6-chloro-2,3-dihydro-1 H -pyrrolo[3,4- c ]pyridine-7-carbonitrilam, through the formation of intermediate 2-{2-hydroxy-2-[3(4)-nitrophenyl]-4-cyano-5alkoxy-1,2-dihydro-3 H -pyrrole-3-ylidene}malononitriles, which can be isolated in low yield. Carrying out the reaction in an aqueous-alcoholic medium makes it possible to obtain 4-amino-1-hydroxy-1-[3(4)-nitrophenyl]3-oxo-6-chloro-2,3-dihydro-1 H -pyrrolo[3,4- c ]pyridine-7-carbonitriles.

In order to study the possibility of creating new anisotropic nanocomposites based on organic molecules containing mercapto groups for specific interaction with nanoparticles, the possibility of converting hydroxy derivatives of polyphenylenes into the corresponding thiols was studied.

A series of phosphorylated quaternary ammonium salts 2-7 with higher alkyl substituents at the quaternary nitrogen atom was obtained using a two-stage synthesis procedure. Compounds 2-5 were found to exhibit high antimicrobial activity against bacterial strains B. cereus , S. aureus , E. coli , as well as fungi Candida albicans . Compounds 6 and 7 containing hexa- and octadecyl substituents at the nitrogen atom are not active against pathogenic strains of microorganisms. Using the ³¹Р NMR method, it was proved that the compounds obtained under the action of air moisture are converted into the corresponding phosphorylated betaines.

(4-Methoxyphenyl)di(pyrrolidin-1-yl)phosphine sulfides were synthesized by reaction of Lausson’s reagent with cyclic amines. It was shown for the first time that phosphine sulfides react with aryl sulfonylazides when boiled in 1,4-dioxane with the elimination of nitrogen and elemental sulfur molecules and the formation of previously undescribed dicycloaminophosphoranylidene sulfonamides.