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New azaadamantane derivatives containing 8-hydroxyquinoline fragments were synthesized. Their antibacterial activity was studied. The synthesized compounds exhibited high antibacterial activity in vitro. The 6-oxo-5,7-diethyl- and 5,7-dimethyl-2-(8'-hydroxyquinolyl-5')-1,3-diazaadamantane dihydrochlorides showed therapeutic effects in mice with dysentery and staphylococcal infections.

Reactions of N-substituted 2-imino-2,5-dihydrofuran-3-carboxamides with thiosemicarbazide gave their new polyconjugated derivatives containing a thiourea fragment. Further condensation of these compounds with ethyl chloroacetate involved closure of thiazolidine ring with the formation of dinuclear polyconjugated heterocyclic systems. The synthesized compounds showed moderate to good antibacterial activity against gram-positive (Staphylococcus aureus 209p, Bacilus subtilis) and gram-negative bacteria (Shigella Flexneri 6858, Escherichia coli 0-55) which was lower than the activity of furazolidone.

ring were successfully synthesized based on thiosemicarbazones of 3-acetyl-2-oxo-2,5-dihydrofurans. The synthesized compounds exhibited moderate to defined antibacterial activities against Gram-positive (Staphylococcus aureus 209P and 1) and Gram-negative (Shigella Flexneri 6858, Esherichia coli 0–55) bacteria compared to furazolidone.

Reactions of 5-(1,4-benzodioxan-2-yl)-1,3,4-oxadiazole-2-thiol with N-substituted chloroacetamides gave a series of the corresponding derivatives at the sulfur atom. Addition reactions of 5-(1,4-benzodioxan-2-yl)-1,3,4-oxadiazole-2-thiol to the C=C double bond of acrylonitrile, acrylamide, and ethyl acrylate, as well as Mannich condensation with morpholine and piperidine, were studied. The synthesized compounds were evaluated for their antibacterial activity.

New azomethines (Schiff bases) containing azaadamantane groups on one side and several biologically active compounds on the other were synthesized. The antibacterial activity of their dihydrochlorides showed that azomethines containing a nitrofuryl group were most active.

The reaction of 5-(1,4-benzodioxan-2-yl)-4H-1,2,4-triazole-3-thiol with N-substituted chloroacetic acid amides obtained by condensation of chloroacetyl chloride with various primary amines furnished a series of S-amidomethyl derivatives. The corresponding thiazolotriazolone prepared from 2-[5-(1,4-benzodioxan-2-yl)-4H-1,2,4-triazol-3-ylthio]acetic acid reacted with aromatic aldehydes to form arylidene derivatives.

A series of β-p-toluylacrylate salts with various amines that retained the molecular fragment responsible for the antibacterial activity were synthesized. A new efficient method for obtaining β-aroylvinyl-1-pyridinium and -triphenylphosphonium bromides was proposed. Antibacterial testing showed that all investigated compounds possessed antibacterial properties.

Interaction of 1-dimethylamino-4-diethylaminobutyn-2, 1-dimethylamino-4-piperidinobutyn-2, and 1-dimethylamino-4-morpholinobutyn-2 with the corresponding alkyl esters of monobromo(chloro)acetic acid was used to synthesize novel monoammonium salts. Studies of the antimicrobial activity of the resulting compounds showed that salts containing hydrophobic alkoxycarbonylmethyl radicals had marked antibacterial activity against Gram-positive and Gram-negative microorganisms.

Aminomethylation and cyanoethylation reactions of 5-(4-alkoxybenzyl)-4-methyl(phenyl, allyl)-4H-1,2,4-triazole-3-thiols have been investigated. According to NMR spectroscopy data, the reactions occur at the nitrogen atom Ν2. The effect of the synthesized compounds on cancer DNA methylation has been evaluated.

In reaction of 6-aminouracyles with ethyl oxochloroacetate ethyl 2-(6-amino-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-oxoacetates were obtained, which by further reaction with various amines afforded oxo(pyrimidinyl)acetamides. According to the data of biological tests, the synthesized compounds showed low antibacterial and antitumor activity.

N-Aroyl-α-aminoacrylic acid 2-(dialkylamino)alkylamides and their quaternary ammonium salts were synthesized and their physicochemical properties were determined. Results obtained from studies of their interactions with human erythrocyte acetylcholinesterase (AChE) and plasma butyrylcholinesterase (BChE) are presented. IC50 values (concentrations producing 50% inhibition of the rate of cholinesterase hydrolysis of 0.1 mM acetylthiocholine) were determined for all the compounds synthesized. The results show that all the compounds synthesized had anticholinesterase properties, mainly specific in relation to BChE. Data on the antibacterial properties of the synthesized compounds are also presented.

1-(4-Substituted phenyl)-2-phenylethanones were aminomethylated with paraformaldehyde and amine in ethanol to produce α-phenyl-β-amino-4-substituted propiophenones. Interaction of these with Grignard reagents in ether yielded tertiary aminopropan-1-ols and their hydrochlorides. Quite efficient inhibition, at differing levels, of adenosine deaminase (ADA, E.C. 3.5.44), one of the key enzymes in purine metabolism, by the compounds synthesized here was demonstrated. A structure-activity relationship was found for ADA inhibition. Most of the compounds synthesized here were found to lack antibacterial activity; only compounds Va, Vd, and VId displayed moderate levels of antibacterial activity against Gram-positive microorganisms.

A series of new 3,4,5-substituted 1,2,4-triazoles were synthesized. Their SH-alkylation by various alkylating compounds and aminomethylation leading to the formation of Mannich bases were studied. The influence of the synthesized compounds on the level of DNA methylation and their antitumor and antibacterial properties were investigated. Several compounds with pronounced demethylation and weak antitumor and antibacterial activities were identified. Correlations among the investigated biological properties were not found.

Interaction of ethylcyano(2,2-dimethyltetrahydro-2H-puran-4-yl)acetate with 3-trifluoromethylphenylmagnesium bromide yielded cyanoesters, decarbethoxylation of which produced the corresponding nitrile. Reduction of the latter with LiAlH4 led to the formation of 2-[2,2-dimethyl-4-(3-trimethylphenyl)tetrahydropyran-4-yl]ethylamine. Interaction of the resulting amine with aromatic aldehydes produced azomethines, which were reduced with NaBH4 to secondary amines, which were then converted to the oxalates. Several of these were found to have high levels of antibacterial activity.

Proceeding from 3-(4-methyl-6-oxo-2-phenyl-1,6-dihydro-5-pyrimidinyl)propanoic and 2-methylpropanoic acids by successive reactions of chlorination, amination, and heterocyclization 4-amino-substituted pyrimidines were synthesized: 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine derivatives and 4-methyl-2-phenyl-5,6-dihydrobenzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidine which we had previously obtained by alternative method. Antibacterial properties of the synthesized compounds were studied.

Synthesis of 3-(4-fluorophenyl)-3-furan-2-ylpropionyl chloride has been performed, and selected transformations of the product have been studied.

Heating a mixture of substituted malonic esters and 6-methoxy-1,3-benzothiazolyl-2-amine afforded new derivatives of benzo[4,5]thiazolo[3,2-a]pyrimidine, 3-substituted 2-hydroxy-4H-benzo[4,5]-thiazolo[3,2-a]pyrimidine-4-ones. The choice between the possible tautomers was carried out basing on the X-ray diffraction analysis of 3-formyl-2-chloro derivative synthesized by formylation of unsubstituted heterocycle by Vilsmeier reaction.

Hydrolysis of 3-(4-isopropoxyphenyl)-3-(2-methoxyphenyl)propionitrile results in 3-(4-isopropoxyphenyl)-3-(2-methoxyphenyl)propionic acid, which after reaction with thionyl chloride is turned into acylchloride. By acylation of a number of amines by 3-(4-isopropoxyphenyl)-3-(2-methoxyphenyl)propionyl chloride, synthesized the corresponding propionamides. The results of biological tests showed that the obtained compounds possess week antibacterial activity.

A number of new 1,3-diazaadamantane derivatives containing quinoline fragments on C2 have been synthesized by condensation of 1,5-dialkyl-3,7-diazabicyclo[3.3.1]nonan-9-one, 1,5-dimethyl-3,7-diazabicyclo-[3.3.1]nonan-9-ol, and 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane with 2-oxo-1,2-dihydroquinoline-3-carbaldehyde, 2-chloro- and 2-iodoquinoline-3-carbaldehyde, and quinoline-2-carbaldehyde.

We report here the synthesis of methyl esters of 5-(1H-1,2,4-triazol-3-ylsulfanylmethyl)furan-2-carboxylic acids containing an alkyl or 2(4)-alkoxyphenyl substituent in position 5 of the triazole ring. Alkaline hydrolysis of these esters yielded the corresponding acids. X-ray diffraction studies showed that the oscillating hydrogen atom in the triazole ring of the methyl ester of 5-[5-(2-ethoxyphenyl)-1H-1,2,4-triazol-3-ylsulfanylmethyl] furyl-2-carboxylic acid was located on the N1 atom. The antibacterial properties of the esters and acids were studied.

The reaction of cyano(2-isopropyltetrahydropyran-4-ylidene)acetic acid ethyl ester and 4-fluorophenylmagnesium bromide produced the cyanoester that was decarboxylated to the corresponding nitrile. Reduction of the latter by LiAlH4 formed 2-[4-(4-fluorophenyl)-2-isopropyltetrahydropyran-4-yl]ethylamine, reaction of which with aromatic aldehydes synthesized azomethines that were then reduced by NaBH4 to secondary amines. The last were transformed to oxalates and acetamides. It was shown that the secondary amine oxalates possessed high antibacterial activity.

The reaction of some aminoalkanols with substituted acetic and propionic acid chlorides was used to synthesize the corresponding (2-dimethylamino-1-methyl and 2-azepan-1-yl)ethyl esters, the methyliodides of which were prepared in order to conduct antibacterial tests of the resulting salts. High antibacterial activity was found for the methyliodides of the aminoalkyl esters of substituted propionic acids, some of which also exhibited strongly pronounced peripheral n-cholinolytic activity.

Uracil and 5-fluoro-, -bromo-, and -iodouracils were alkylated by substituted benzylchlorides to obtain N1-mono- and N 1,N 3-bis-substituted derivatives. The toxicity, antitumor, and antibacterial properties of the synthesized compounds were investigated. It was established that 5-fluoro- and 5-iodouracils exhibited more pronounced antitumor properties than 5-bromouracil derivatives.

A method based on condensed 4-cyanopyridinethiones using O-tosylhydroxylamine as the aminating agent was developed for preparing tosylates of N-amino-derivatives of pyrano[3,4-c]pyridines; 5,6,7,8-tetrahydroisoquinolines; and cyclopenta[c]pyridines. The antibacterial activity of the synthesized compounds was assessed.

Reduction of 3-(4-chlorophenyl)-3-(4-fluorophenyl)propionitrile produced 3-(4-chlorophenyl)-3-(4-fluorophenyl)propylamine, the reaction of which with aromatic and heterocyclic aldehydes and subsequent reduction with NaBH4 yielded [3-(4-chlorophenyl)-3-(4-fluorophenyl)propyl]-substituted amines. Hydrolysis of the corresponding nitrile afforded 3-(4-chlorophenyl)-3-(4-fluorophenyl)propionic acid, acylation of the chloride of which with various amines led to amides that were reduced to amines. The corresponding ammonium oxalates were prepared from the amines. The antibacterial and antioxidant properties of the ammonium oxalates were studied. It was established that some of the compounds exhibited high antibacterial activity but in most cases did not neutralize superoxide radicals.

A series of substituted 6-alkyl(6H)-3-phenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines have been synthesized by reaction of 3-alkyl-4-amino-5-thio-1,2,4-triazoles with substituted phenacylbromides in the presence of an equimolar amount of KOH. Mass spectra for the dissociative ionization by electron impact, antibacterial activity, and antitumor properties of the synthesized compounds have been studied. It was established that some compounds at doses of 50 – 100 mg/kg decrease the growth of sarcomas 45 and 37 by 35 – 47%.

A method has been developed for the synthesis of new heterocyclic compounds containing γ-butanolide fragments. The antibacterial properties of the obtained compounds have been investigated. The tested compounds exhibit moderate antibacterial activity.

The antibacterial activity of 1,3-diazaadamantane derivatives was studied; a degree of relationship between chemical structure and the antibacterial activity of the compounds synthesized was identified. The results obtained here showed that some of the study compounds were active against Gram-positive and Gram-negative microorganisms.

A series of new analogs of 2-arylpyrrolidinecarbonitriles were synthesized under phase-transfer catalysis conditions. New analogs of pyrrolidinecarboxamides were synthesized based on these carbonitriles. Biological evaluation showed that the synthesized derivatives of pyrrolidinecarbonitriles and pyrrolidinecarboxamides possessed moderate anticancer activity.

A method for obtaining derivatives of γ-dilactones, 3-methyl-3-(3′-amino[or substituted amino]thiazol-4-yl)-8-alkoxymethyl-2,7-dioxaspiro[4, 4]nonane-1,6-diones, has been developed. Their antibacterial and antitumor properties have been evaluated. Compounds possessing low toxicity and weak antitumor activity have been found in the series of γ-dilactone derivatives.

Aseries of new 2.5-dihydrofuran derivatives containing cyclohexyl rings have been synthesized. The antibacterial activity of these compounds has been investigated. The experimental results showed that some compounds exhibited moderate antibacterial activity with respect to both Gram-positive and Gram-negative bacterial species.

Aseries of 4-(2-R-vinyl) derivatives of 2,5-dihydrofurans have been synthesized and their antibacterial activity has been investigated. The experimental results showed that the synthesized compounds possess significant antibacterial activity with respect to both Gram-positive and Gram-negative bacterial species.

Aus den Hydraziden (I) und den Isothiocyanaten (II) werden die Thiosemicarbazide (III) hergestellt und zu den Triazolen (IV) cyclisiert, die keine antibakterielle Wirkung gegen Staphylokokken haben.