Diuretics are widely used to treat pathologies of various genesis. However, the development of side effects during their long-term use remains a problem of traditional treatment regimens. The search for diuretics that would be aimed at inhibiting a key target molecule that is involved in the regulation of salt or water balance in the kidney, and certainly have a low level of toxicity and side effects, is an urgent task for researchers. Our preliminary screening of substituted quinones using in silico and in vitro methodology identified a number of effective compounds that outperform or compete with diuretics. The compounds are not "classic" carbonic anhydrase II inhibitors, but the pronounced diuretic effect of a number of compounds requires additional explanation. Therefore, the aim of the work was to study the effect of substituted quinones on the excretory function of rat kidneys to assess the prospects of their further structural modification and use as potential diuretics. Considering the experimental data, it should be noted that compounds AVD-6, AVD-7, AVD-8 and AVD-9 have pronounced diuretic activity. Thus, according to indicators of ex­cretory indices of electrolytes, it is possible to note the predominant influence of compounds AVD-6, AVD-7, AVD-8 and AVD-9 on excretion of sodium, potassium and chlorine from the body. Compounds AVD-6, AVD-7, AVD-8 and AVD-9, in contrast to Hydrochlorothiazide, which blocks carbonic anhydrase in the proximal part of the convoluted tubules and accelerates the excretion of potassium with from the urine, have a much lower excretory index as for these ions. Thus, our conducted research made it possible to identify a new, little-known class of hybrid molecular structures, namely (N'-(4-[(aroyloxy)imino]cyclohexa-2,5-dien-1-ylidene) aroylhydrazides (AVD-6, AVD-7, AVD-8 and AVD-9), which, in addition to affecting the excretory function of the kidneys, have significant diuretic activity and are potential diuretics.

N-substituted 1,4-quinoneimines have a wide spectrum of biological activity. The stabilizing property of N-substituted p-quinonemono- and diimines is known, which is related to their antioxidant activity. Derivatives of N-substituted 1,4-benzoquinoneimines are used as antioxidants and stabilizers. For example, stabilization of fats, oils, unsaturated compounds with N-phenyl-1,4-benzoquinonimine was proposed. The aim of this work was the synthesis and study of the antioxidant activity of N-heterylthio- and N-ethylxanthogenato-1,4-benzoquinoneimines. N-Heterylthio-1,4-benzoquinonimines were synthesized by the reaction of N-chloro-1,4-benzoquino-4-nimines with the corresponding heterocyclic mercaptans in acetone. The reaction of quinonimines with mercaptobenzoxazole was difficult, so it was carried out with the sodium salt of mercaptobenzoxazole in ethyl alcohol. The reaction products were bright orange crystals. The composition and structure of the synthesized compounds was established based on the results of elemental analysis and the study of PMR spectra. An in vitro method based on the reaction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) dissolved in ethanol was used to assess antioxidant activity (AOA). As a result of the reduction of DPPH with an antioxidant, a gradual discoloration of the DPPH solution in ethanol was observed, which was determined by the change in optical density at 517 nm on a spectrophotometer. The radical-absorbing activity (RAP) of the compound was defined as the ratio of the difference in the value of the optical densities of the DPPH solution and the solution containing the test substance and DPPH to the optical density of the DPPH solution. High levels of antioxidant activity were found for 4-(benzo[d]thiazol-2-ylthioimino)-2,5-dimethylcyclohexa-2,5-dienone, 4-(1H-benzo[d]imidazol-2-ylthioimino)-2, 6-dimethylcyclohexa-2,5-dienone, and 2,6-dimethyl-4-[(4H-1,2,4-triazol-5-ylsulfanyl)imino]cyclohexa-2,5-dienone. It was established that 2,6-dimethyl-4-{[(ethoxymethanethioyl)sulfanyl]imino}cyclohexa-2,5-dienone neutralizes free radical by 91% after 20 minutes of interaction with the stable free radical DPPH.

Sokolova K.V., Podpletnia O.A., Konovalova S.O., Avdieienko A.P., Komarovska-Porokhniavets O.Z., Lubenets V.I., Kovalenko S.I. Continuing our research on compounds that affect urination, we have become interested in N-arylsulfonyl-2-aroylamino-1,4-quinone imines, which combine a quinone matrix with tolylsulfonamide and benzamide fragments with versatile biological activity in their structure, which has a promising value in preventing development of pathological processes in kidneys. Therefore, the search for low-toxic compounds with polyvector activity as a promising approach to the design of drug-like molecules has become an urgent aspect in this regard. The aim of this work was to investigate N-arylsulfonyl-2-aroylamino-1,4-quinone imines and their hydrogenated analogues as promising diuretic agents with antiradical and antibacterial activity using in silico, in vitro and in vivo methodologies. The virtual laboratory of the ProTox-II site is used to predict the toxicity of molecules. The study of compounds affecting the excretory function of the rat kidneys was carried out on 120 white Wistar rats according to the method of E.B. Berkhin under conditions of water stress and spontaneous urination. The interaction of the synthesised compounds with 2,2-diphenyl-1-picrylhydrazyl (DPPH) was used to study their antiradical activity in vitro. The antibacterial activity of the compounds was studied on test cultures of the bacteria Escherichia coli, Staphylococcus aureus, Mycobacterium luteum and the fungi Candida tenuis, Aspergillus niger by the method of serial dilutions in a liquid nutrient medium. Based on the results of the calculation, it was predicted that N-arylsulfonyl-2-aroylamino-1,4-quinone imines (2) and their hydrogenated analogues (3) have hepato-(immuno-, cyto-) toxicity, carcinogenicity (mutagenicity) similar to natural quinones and diuretics (toxicity class IV). This class of compounds has been shown to have both stimulatory and inhibitory effects on diuresis under condi­tions of water stress and spontaneous urination. At the same time, N-(5-methyl-6-oxo-3-(tosylimino)cyclohexa-1,4-dien-1-yl)benzamide (2.3) was revealed to increase daily diuresis by 67.1% compared with the control, exceeding the effect of «Furosemide» (22.2%). It was found that quinone imines (2.1-2.5) inhibited the formation of the DPPH radical by 25.99-40.09%, while their hydrogenated analogues (3.1 and 3.2) – by 61.56% and 68.28%, respectively, and are more effective acceptors of radicals. The microbiological screening revealed a number of promising compounds that inhibited the growth of S. aureus (compound 2.5, MIC 62.5 μg/ml, MBC 125.0 μg/ml), M. luteum (3.1 and 3.2, MIC 31.2 μg/ml, MBC 62.5 μg/ml) and A. niger (2.1, 2.4 and 3.2, MIC 31.2 μg/ml, MPC 62.5 μg/ml). According to the results of biological studies, among N-arylsulfonyl-2-aroylamino-1,4-quinone imines and their hydrogenated analogues, compound 2.3 has been iden­tified, which competes with «Furosemide» in potency and has high antibacterial activity against S. aureus. Other compounds show moderate antiradical activity, high antibacterial activity against M. luteum (2.1, 3.1) and antifungal activity against A. niger (2.1, 2.4, 3.2). The obtained results support the further research for diuretics with polyvector activity within this class of compounds.

It was established that in the solutions of N-[arylsulfonylimino(phenyl)methyl]-1,4-benzoquinonemonoimines there are both Z,E-isomerization relative to C=N bonds and atropoisomerism (inhibited rotation around the =N1–C= bond). The latter can be detected when there are the diastereotopic isopropyl groups in the quinoid ring. The rate constants of this process were calculated by the method of analysis of the full line in the 1H NMR spectra. Activation thermodynamic parameters were determined on their basis. With the help of quantum-chemical calculations, we proved that the determined experimental barriers corresponded exactly to the inhibited rotation around the bond =N1–C=.

The design and search for new selective inhibitors of CA II with a better pharmacological profile, which would cause minimal electrolyte disturbances in the body, remains an urgent problem of medical chemistry and pharmacology today. It is important that the discovered new classes of inhibitors do not always contain the main “pharmacophoric” function (sulfamide), which is characteristic of “classic” drugs (Acetazolamide, Methazolamide, Ethoxzolamide, Dorzolamide and others), but are derivatives of phenols, polyamines, coumarins/thiocoumarins, ureas, thioureas, hydroxamates, etc. These molecules also bind in the active site of the enzyme, but do not interact directly with the catalytic zinc ion or interact through zinc-coordinated water molecules/hydroxide ion. However, this leads to an increase in their selectivity and, as a result, pharmacological action. Continuing the search for compounds that affect urination, we were interested in aroylhydrazones of esters of quinone oxime. Firstly, they are characterized by certain structural features (dynamic and geometric isomerism); secondly, they exhibit redox properties; thirdly, the presence of aromatic fragments makes it possible to create a voluminous combinatorial library for analysis. These compounds are ligands in complexation reactions, and an additional increase in the number of hydrogen acceptors in the molecule due to structural modification will improve ligand-enzymatic interactions with carbonic anhydrase (CAII) and, as a result, reveal new promising diuretics. The aim – design and search for potential diuretics (CA II inhibitors) among aroylhydrazones of esters of quinone oxime using in silico, traditional synthesis and in vivo methodologies. Methods of organic synthesis, physico-chemical methods of analysis of organic compounds (NMR 1H-spectroscopy, elemental analysis). Prediction of affinity to the biological target, prediction of toxicity and lipophilicity of the combinatorial library of benzohydrazides O-aroyl esters of quinone oxime using computer services. The study of compounds affecting the excretory function of rat kidneys was carried out according to the generally accepted method of E.B.Berkhin with water load. The investigation of the probable mechanism was carried out using flexible molecular docking, as an approach to search for molecules that have affinity for human carbonic anhydrase type II (CA II). Macromolecular data of the crystal structure of CA II (PDB ID – 3HS4) were downloaded from the Protein Data Bank (PDB). The design was developed and the search for diuretic agents among benzohydrazides of O-aroyl esters of quinone oximes was developed using in silico methods (prediction of affinity, lipophilicity, toxicity and enzyme-ligand interactions), traditional organic synthesis, and in vivo methods (effect on excretory function of rat kidneys). The synthesis of benzohydrazides of O-aroyl esters of quinone oxime was carried out by the interaction of aroylhydrazines with 4-[(aroylimino)]cyclohexa-2,5-dien-1-ones. The structure of the synthesized compounds was confirmed by elemental analysis and 1H NMR spectra. Studies of the effect of synthesized compounds on the excretory function of rat kidneys allowed us to identify a number of promising compounds among aroylhydrazones of quinonexime esters, which increase daily diuresis by 54.2-352.8% compared to the control group. At the same time, it was established that the most active was N'-(4-[(2-chlorobenzoyloxy)imino]cyclohexa-2,5-dien-1-ylidene)-3-nitrobenzohydrazide, which increased daily diuresis by 352.8% in comparison with the control group, while exceeding the effect of “Hydrochlorothiazide” (170.8%). The developed and implemented strategy for the search for diuretics among benzohydrazides of O-aroylesters of quinone oxime allowed the identification of an effective compound, which in terms of diuretic effect exceeds the comparison drug “Hydrochlorothiazide”. Visualization of the molecular docking of the active compounds showed that their geometry makes it difficult to place them in the pocket of the active site of CA II, but the pronounced diuretic effect can also be associated with their ability to form coordination bonds with the zinc cation. The obtained results justify the further targeted search for potential diuretics among this class of compounds for a more detailed understanding and study of the mechanism of action.

Reactions of (chlorosulfanyl)benzenes with benzene-1,4-diamines afforded new N,N′-bis(arylsul­fanyl)cyclohexa-2,5-diene-1,4-diimines which were oxidized to N,N′-(cyclohexa-2,5-diene-1,4-diylidene)­bis(arenesulfinamides) with 2 equiv of m-chloroperoxybenzoic acid. When the oxidation was carried out using 4 equiv of m-chloroperoxybenzoic acid, the corresponding bis-sulfonamides were obtained. The synthesized compounds were predicted in silico to exhibit biological activity with a high probability.

Modern cameras, desktop scanners, smartphones allow not only registering an image, but also determining its color characteristics. That allows us to quickly, objectively and automatically determine the color characteristics of colored samples in acid-base titration, because there is a significant error at visually determining the pH range of the color transition. In analytical chemistry the characteristics of acid-base indicators are very important, in particular their pH transition interval. But the disadvantage of most indicators is the wide range of color transition: from 1 to 3 pH units. The aim of this work is to find new acid-base indicators that change color in an alkaline environment and have a narrow pH range of the color transition. We have developed the apparatus and technique of convenient and highprecision simultaneous determination of the pH of the medium and the color of the acidbase indicators. In acid-base titration the PH measurements were performed with a combined glass electrode AD1131 by рН-meter AD1000. The color transition was determined with help of a smartphone with the subsequent processing of the results by computer software. The color characteristics were measured for each channel of the RGB model in the range from 0 to 255. Our apparatus is small and mobile, and allows us simultaneously to measure the pH of the medium and accurately to determine the color characteristics. As a result, we can construct graphical dependencies of color on pH for each channel of the RGB model. We found the N-arylsulfonyl-2-aroylamido-1,4-benzo(naphto)quinone monoimines and 2,5-dibenzoylamido-1,4-benzoquinone are good acid-base indicators. They “work” in the pH range from 8.82 to 11.35 and have a very narrow color transition interval from 0.10 to 0.61. Solutions of these compounds in an alkaline medium have bright intense colors due to formation of mesomeric ions. That allows using of these indicators in the titration of weak acids with strong bases and vice versa by the method of neutralization.

N-{3-[(4-Methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dien-1-yl}arylamides and their derivatives were synthesized by the reaction of the corresponding N-(4-oxocyclohexa-2,5-dien-1-ylidene)arylsulfonamides with N-chloramides. The biological activity of the synthesized compounds was studied on test cultures of Escherichia coli 67, Staphylococcus aureus 209-p, Mycobacterium luteum VKM B-868 and fungi Candida tenuis VKM Y-70, Aspergillus niger VKM F-1119 by the method of diffusion of substances into agar on a solid nutrient medium. The degree of activity of the test compounds was determined by the diameter of the zones of inhibition of growth of test cultures of microorganisms. The minimum inhibitory, bactericidal and fungicidal concentrations were determined by the method of serial dilutions of the substance in a liquid nutrient medium. At the studied concentration, the method of diffusion of substances into agar on a solid nutrient medium has shown that these compounds have low activity against bacteria Escherichia coli, Staphylococcus aureus, Mycobacterium luteum and fungi Candida tenuis, Aspergillus niger. The diameters of the zones of inhibition of growth of test cultures of microorganisms were less than 15 mm. In research by the method of serial dilutions of the substance in a liquid nutrient medium, they have been found to have bactericidal and fungicidal activity. The minimum inhibitory concentration of N-{2-hydroxy-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}benzamide was 31.2 μg/ml against bacteria Mycobacterium luteum. The minimum inhibitory concentration of N-{2-hydroxy-3-methyl-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}benzamide against fungi Aspergillus niger was 31.2 μg/ml. The minimum bactericidal concentration of N-{2-hydroxy-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}benzamide was 62.5 μg/ml against bacteria Mycobacterium luteum. Minimum fungicidal concentration of N-{3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dien-1-yl}benzamide and N-{2-hydroxy-3-methyl-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}benzamide was 62.5 μg/ml in action to mold fungi Aspergillus niger.

The efficiency of cold steel rolling depends mainly on the quality of the metal-working coolant (MWC) and its cost. In this connection, it is actual to search for new compositions of lubricants and emulsions, which provide the lowest values of the friction coefficients in deformation zone and are obtained by waste recycling in other industries. In this study we have developed new compositions of the MWC on basis of mono- and diglycerides and their esters of boric acid synthesized from the wastes of sunflower oil production. The new compositions of MWC were tested in DSEA on laboratory rolling mill 100x100 with a roll diameter of 100 mm. The efficiency of new MWC during cold rolling of brass L63 samples was determined by factor of metal stretch forming λ . We found the new metal-working coolants to show the most efficiency under higher cobbing that provides the highest metal stretch forming. The composition with 30 % of mono- and diglycerides is the most effective because it provides the minimum coefficient of friction that leads to increase of factor of metal stretch forming. Thereby the metal-working coolants on basis of mono- and diglycerides obtained from the wastes of sunflower oil production can be recommended for use in strip rolling of copper-zinc alloys because of a low cost, availability and high efficiency.

Hydrazones of 1,4-benzoquinone, which have a wide range of biological activities, can be synthesized in the reactions of 4-{[(arylsulfonyl)oxy]imino}cyclohexa-2,5-diene-1-ones or N-(4-oxocyclohexa-2,5-diene-1-ylidene)arylsulfonamides with N-substituted hydrazines. In this study, the reaction of 2,6-disubstituted 4-{[(tolyl(methane)sulfonyl)oxy]imino}cyclohexa-2,5-diene-1-ones with aroylhydrazides gave N'-(3,5-dialkyl-4-oxocyclohexa-2,5-diene-1-ylidene)aroylhydrazides, which can be obtained by cross-synthesis in the reaction of N-(3,5-dialkyl-4-oxocyclohexa-2,5-dien-1-ylidene)arylsulfonamides with aroylhydrazides. As a result of the reaction of 4-{[(tolyl(methane)sulfonyl)oxy]imino}cyclohexa-2,5-dien-1-ones with phenylhydrazine, stable 4-hydroxyanilinium tolyl(methane)sulfates were isolated. Their structures were confirmed by X-ray diffraction data. We suggested that at the first stage of the reaction between 4-{[(tolyl(methane)sulfonyl)oxy]imino}cyclohexa-2,5-diene-1-ones and hydrazines, the N–O bond of starting 4-(oxyimino)cyclohexa-2,5-diene-1-one was broken forming sulfonic acid and corresponding quinoneimine. The latter either can be reduced to corresponding aminophenol under reaction conditions or can react with an excess of N-substituted hydrazine yielding corresponding hydrazide. The formation of N'-(4-oxocyclohexa-2,5-diene-1-ylidene)arohydrazides is facilitated by a lower basicity of hydrazide and a lower redox potential of quinoneimine.

Halogenation of N ′-(arenesulfonyl)- N -[2,6(3,5)-dialkyl-4-oxocyclohexa-2,5-dien-1-ylidene]benzenecarboximidamides and their reduction products gave derivatives containing up to four halogen atoms. The degree of halogenation can be controlled by variation of the reaction conditions only in the reactions with 2,6(3,5)dimethyl derivatives. The maximum number of halogen atoms were introduced into 2,6(3,5)-dimethyl- and 3,5-diisopropyl-substituted substrates. The presence of bulky tert -butyl groups in the quinoid ring significantly reduced the degree of halogenation, and halogen molecule added to only one C=C double bond of the quinoid ring. The axial orientation of alkyl substituents in the cyclohexene products suggests syn addition of halogens to the C=C double bond of the quinoid ring.

N-{3-[(Aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamides have been synthesized by the reaction of the corresponding N-(4-oxocyclohexa-2,5-diene-1-ylidene)arylsulfonamides with N-chloramides with a ratio of reagents 1:2 in a solution of propan-2-one in the presence of triethylamine. The products of addition of hydrogen halides with the entry of halogen atoms in position 4 or 5 of the quinoid ring have been obtained as a result of hydrochlorination and hydrobromination of N-{3-[(aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamides. The possibility of hydrohalogenation and thiocyanation of these benzamides is determined by a steric factor. The presence of bulk substituents in the quinoid ring does not allow the introduction of a halogen atom in the 2 position of the quinoid ring. The product of aromatization of the quinoid cycle, N-{2-hydroxy-3,4-dimethyl-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}-4-methylbenzamide, was only obtained as a result of the action of hydrogen halides on 4-methyl-N-{4,5-dimethyl-3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamide. The thiocyanate ion addition product was obtained only for 4-chloro-N-{4-methyl-3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamide, which has a free ortho-position relative to the carbonyl carbon of the quinoid ring. The activities Insulysin inhibitor, CTGF expression inhibitor, Glutamyl endopeptidase II inhibitor, Transcription factor STAT3 inhibitor are possible for the products of hydrohalogenation and thiocyanation of N-{3-[(aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamides.

The acylamination of the N-substituted 1,4-benzoquinonimines is a simple method to enter the acylaminogroup into the quinoid ring. In this way, the final product with the unchangeable quinoid structure can be obtained in one stage. The acylamination was carried out as reaction of N-arylsulfonyl-1,4-benzoquinone monoimines and N-chloramide of 4-methylbenzoic acid. The starting N-arylsulfonyl-1,4-benzoquinone monoimines contained both donor and acceptor substituents in the quinoid ring. As a result, 2-(4-methylbenzoyl)amino-N-(4-methylphenyl) sulfonyl-1,4-benzoquinone monoimines were obtained. These monoimines are the products of substitution of the hydrogen atom of the free C=C bond of the quinoid ring of the starting quinone monoimine by the acylamino group. The nature of the substituent in the quinoid ring of the starting N-arylsulfonyl-1,4-benzoquinone monoimines does not influence on the reaction direction. The direction of the reaction depends on the first stage, and this reaction can be regarded as a 1,4-addition. The possibility of this reaction is determined by the steric factor. The same 2-(4-methylbenzoyl)amino-N-(4-methylphenyl)sulfonyl-1,4-benzoquinone monoimines were obtained in reaction of N-arylsulfonyl-1,4-benzoquinone monoamines with O-(4-methyl)benzoylbenzhydroxamic acid in the presence of potassium acetate. The first stage of this reaction is the formation of an anion of hydroxamic acid under the action of acetate anion. Thereafter, the anion is added to the free C=C bond of the quinoid ring. formation of the final product. The PASS program was used to analyze the potential biological activities of the synthetic compounds. All products were found to be inhibitory to the enzymes Glutamyl endopeptidase II, Insulysin, Hexokinase, and Omptin.

Indole derivatives are an essential elements of many natural and synthetic compounds having significant biological activity. New derivatives of 2,3-dimethylindole were synthesized in this work by the reaction of N-(4-oxocyclohexa-2,5-dien-1-ylidene)arylsulfon(aroyl)amides and 4-methyl-N-(4-oxonaphthalen-1(4H)-ylidene)benzene-1-sulfonamide with 2,3-dimethylindole. The possibility of these reactions is determined by the redox potential of the starting amides and steric factor. If there is a free C=C bond in the quinoid ring of the starting arylsulfonamides, the reaction proceeds under the 1,4-addition scheme with the formation of corresponding N-[3-(2,3-dimethyl-1H-indol-1-yl)-4-hydroxyphenyl(naphthyl-1)]arylsulfonamides which are potentially biologically active compounds. N-(4-Oxocyclohexa-2,5-diene-1-ylidene)aroylamides have a high redox potential as compared with similar arylsulfonamides and naphthalene derivatives; therefore, two processes proceed in their reaction with 2,3-dimethylindole: reduction and 1,4-addition. The 1,4-addition product was obtained only for the 2,3-dimethyl derivative, which has the lowest redox potential among the investigated aroylamides. Analysis of the potential biological activity of the synthesized compounds by using the PASS program showed that the synthesized products can exhibit the following activities: para amino benzoic acid antagonist, glutamyl endopeptidase II inhibitor, CYP3A2 substrate, insulysin inhibitor, membrane integrity agonist and phobic disorders treatment.

Aroylhydrazones contain the active pharmacophore group >C=N–NH–CO–. These compounds show antimicrobial, antibacterial, and even anticancer activity. In addition, aroylhydrazones are synthons in the synthesis of various heterocyclic compounds. The purpose of this work is to define the features of the reaction of aryl(benzoyl)hydrazines with O-sulfonates of 1,4-quinone monooxime and to synthesize the benzoquinone hydrazones based on them. In the result of reaction of 1,4-quinone monoxime O-sulfonates with phenylhydrazine the p-tolyl(methyl)sulfates of the corresponding aminophenols were obtained. Subsequent treatment of these sulfates with water and acidification led to sulfate destruction and formation of a mixture of the corresponding aminophenol and p-tolyl(methyl)sulfate acid. We did not obtain 1,4-benzoquinone hydrazones. Thus, in the reaction of 1,4-quinone monoxime O-sulfonates with phenylhydrazine, the first stage is the N–O bond break with reduction of quinoid ring, and this redox process is due to the high basicity of aryl hydrazines. The aroylhydrazones of 1,4-benzoquinone were obtained only in the reaction of aroylhydrazines with 1,4-quinone monoxime O-sulfonates, containing two alkyl substituents in the both orthopositions to the carbonyl group of the quinoid ring. The first step of this reaction is also the =N–O– bond breaking of the starting sulfonates and formation of corresponding quinone imines. 2,6-Disubstituted quinone monoimines have less redox potential, and aroylhydrazines are less basic than arylhydrazines, therefore, the formation of corresponding aroylhydrazones of 1,4-benzoquinone is possible. The variation of the substituent attached to the oxygen atom of the starting 1,4-quinone monooxime O-sulfonates (MeSO2 or Ts) does not affect the reaction route.

N-{3-[(Aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamides have been synthesized by the reaction of the corresponding N-(4-oxocyclohexa-2,5-diene-1-ylidene)arylsulfonamides with N-chloramides with a ratio of reagents 1:2 in a solution of propan-2-one in the presence of triethylamine. The products of addition of hydrogen halides with the entry of halogen atoms in position 4 or 5 of the quinoid ring have been obtained as a result of hydrochlorination and hydrobromination of N-{3-[(aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamides. The possibility of hydrohalogenation and thiocyanation of these benzamides is determined by a steric factor. The presence of bulk substituents in the quinoid ring does not allow the introduction of a halogen atom in the 2 position of the quinoid ring. The product of aromatization of the quinoid cycle, N-{2-hydroxy-3,4-dimethyl-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}-4-methylbenzamide, was only obtained as a result of the action of hydrogen halides on 4-methyl-N-{4,5-dimethyl-3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamide. The thiocyanate ion addition product was obtained only for 4-chloro-N-{4-methyl-3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamide,which has a free ortho-position relative to the carbonyl carbon of the quinoid ring. The activities Insulysin inhibitor, CTGF expression inhibitor, Glutamyl endopeptidase II inhibitor, Transcription factor STAT3 inhibitor are possible for the products of hydrohalogenation and thiocyanation of N-{3-[(aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamides.

В результаті реакції N-арилсульфоніл-1,4-бензохінонмоноімінів з замісниками в хіноїдному ядрі з N-хлорамідом 4-метилбензойної кислоти і N-(бензоїлокси)-4-метилбензамідом отримано продукти заміщення атому Гідрогену вільного С=С зв’язку хіноїдного ядра вихідного хінонмоноіміну на ациламіногрупу. Природа замісника в хіноїдному ядрі хіноніміну не впливає на напрямок реакції, який визначається першою стадією і яку можна розглядати як 1,4-приєднання. Можливість перебігу цієї реакції визначається стеричним фактором.