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A series of disperse dyes, 9,10-anthraquinone containing dithiocarbamate, thiourea and triazole fragments, were prepared via consecutive refunctionalization of aminoanthraquinones in our previous studies and their structures were confirmed by the 1H, 13C NMR, IR spectra, LC-MS and elemental analysis data. The obtained compounds were applied on polyester fabrics by the exhaustion method at 130°C at pH 4.0-5.0, and their dyeing properties were evaluated by color measurements, the washing fastness test and the light fastness test. Many of these dyes gave solid and level dyeings on polyester fabric with low % concentration of dye. The dyed samples displayed very good color fastnesses. The color change and staining test results were quite good with ratings of “4-5” or above. The light fastness test results were also satisfactory for the most of the dyed samples.

A preparatively convenient one-pot method for the synthesis of new 7-thioxo[1,3]thiazolo[3,2-c]pyrimidine derivatives 3a–3l by the cyclocondensation of 5-methyl(1,3-thiazolidin-2-ylidene)ketones 1a...

9,10-Anthracenediones an important class among quinonic compounds of natural and synthetic origin with many applications. Amino- and diaminosubstituted 9,10-anthracenediones are one of the main classes among 9,10-anthracenedione derivatives. Primarily, they are the key structures for obtaining various dyes. Besides applying their dye properties, aminoanthracenediones became the objects for searching for new biologically active compounds with antibacterial, antifungal, anticancer, antioxidant, antiviral, immunostimulating, and antiprotozoal activity in medical chemistry. However, amino- and diamino-substituted 9,10-anthracenediones are widely used as analytical reagents, color, and metal indicators. Areas of the practical application of these compounds are constantly expanding. This mini-review dedicates the advantages of amino- and diamino-9,10-anthracenediones derivatives as biologically active compounds and substances with applied application in various fields.

The ketene dithioacetal 3 generated from 2-nitroperchlorobutadiene 1 reacted with various heterocyclic amines and aliphatic, aromatic and heterocyclic thiols to produce functionalized new ketene-N,S,S-acetals and S,S,S-acetals 4a-f, 5a-h as heterocyclic dithiolanes. They were separated/purified by chromatographic methods and their exact structure characterization were made clear by spectroscopic methods. These compounds synthesized could act as effective drugs for versatile activity. Evaluation of the antimicrobial effect of the obtained substances determined derivatives 4e and 5h, which have MIC=15.6 μg/mL for the test culture of Mycobacterium luteum bacteria closing to the control drug Vancomycin. The obtained compounds can be proposed as a promising synthetic objects for future molecular design to enhance the antimicrobial action. Ketene dithioacetals 3, 4a, 4b, 4e, 5g (50 mg/kg) exhibited antiseizure effect comparable with reference drug (valproic acid) on the model of pentylenetetrazole-induced convulsions after single oral administration both at 3 h and 24 h. Furthermore, tested dithioacetals possessed prolonged antidepressant activity in forced swim test (FST) considerable decreasing the duration of immobility time compared to reference drug amitriptyline. This is the first study of the investigation of anticonvulsant and antidepressant activities of ketene dithioacetals.

The analysis of the biological potential of derivatives of 4-alkenyl- and imino functionalized pyrazoles is carried out, based on which the expediency of design of new structures with pharmacophore 5-(4-nitrophenyl)furanyl fragment is substantiated. Their synthesis method using a structural modification of 3-[5-(4-nitrophenyl)furan-2-yl]pyrazole-4-carbaldehyde to the corresponding alkenyl derivatives under the action of malononitrile, ethyl cyanoacetate, cyanoacetamide, and thioxoimidazolidine is proposed. The hydrazones, (thio)semicarbazones, and oximes were obtained by the condensation of corresponding aldehydes with hydrazides, (thio)semicarbazides, and hydroxylamine. The synthesized compounds' composition and structure were determined by elemental analysis, IR, and 1H NMR spectra. The fact existence of a mixture of E/Z-isomers among the series of obtained hydrazones of 1-phenyl-4-pyrazolecarbaldehydes was determined, and the quantitative ratio of geometric isomers was determined using 1H NMR spectroscopy data. The results of the microbiological evaluation of the synthesized pyrazole derivatives showed that they have a pronounced effect on strains of bacteria S. aureus ATCC 25923, E. coli ATCC 25922, and fungi of the genus Candida and are promising for the creation of effective antimicrobial agents.

For the first time, the literature sources concerning the chemical transformations of diazonium salts of 1(2)-amino-9,10-anthracenediones are generalized and systematized. The potential of 9,10-dioxoanthracenyldiazonium salts as key substrates in the preparation of various linear-functionalized, acyclic and heterocyclic derivatives has been determined. The main synthetic transformations of diazonium salts of amino-9,10-anthracenediones, which are realized without preserving the azo function lead to the formation of reaction products of Sandmeyer, Meerwein, and Gomberg–Bachmann–Hay, are analyzed. The use of 9,10-dioxoanthracenyldiazonium salts or products of their transformations for obtaining heteryl-containing condensed and functionalized derivatives is presented.

Onychomycosis is one of the most acute problems of modern medicine, which accounts for about 50% of all nail diseases. Fungi of dermatophytes of the genus Trichophyton are the most studied etiological factor of onychomycosis. Non-dermatophytes can also cause onychomycosis. Fungi of the genus Aspergillus is one of the main pathogens among the non-dermatophytes agents of onychomycosis. Antifungal nail lacquer is the most optimal dosage form for the topical treatment of onychomycosis. GABA derivative of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide was used as a perspective antifungal agent in the form of lacquer. The antifungal action of the obtained lacquer containing compound 2 against fungus strain Aspergillus niger VKM F-1119 was compared with the known antifungal lacquer “Lamisil” containing terbinafine as the active agent. Investigation of the antifungal action was carried out at concentrations of 1%, 0.5%, and 0.1% of compound 2 and terbinafine using the diffusion in agar technic after 24 h and 72 h. It has been determined that derivative 2, as well as terbinafine at a concentration of 1%, caused fungicidal action after 24 h and fungicidal and fungistatic effect after 72 h.

The global emergence and dissemination of multidrug-resistant fungal and bacterial pathogens is a serious public health threat. The development of novel highly active antimicrobial compounds simultaneously targeting several targets in bacterial or fungal pathogens could help to fight antimicrobial resistance. The four-component one-pot two-step facile synthesis of a new 2-dithiocarbamate-N-(9,10-dioxo-9,10-dihydroanthracenyl)acetamides 3a-n by the interaction of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracenyl)acetamide 1 or 2 with a series of in situ generated potassium salt of dithiocarbamic acids in DMF-H2O is presented. Evaluation of the antimicrobial activity of the synthesized compounds against bacteria strains Escherichia coli В-906, Staphylococcus aureus 209-Р, Mycobacterium luteumВ-917, and fungi Candida tenuis VKM Y-70, Aspergillus niger VKM F-1119 has been carried out by the diffusion in agar method and by the serial dilution technique. It has been established that synthesized compounds 3a, 3i, 3j have the good antibacterial activity against strain M. luteum at a concentration of 0.5% and the dithiocarbamates 3b, 3i, 3j, 3n demonstrate antifungal effect against C. tenuis at the same concentration. The results of the serial dilution technique showed that compound 3j has high antibacterial action at MIC 3.9 μg/ml.

Researches with nitro compounds mainly relates to the synthesis of their derivatives used as unusual intermediate compounds. Because of their high reactivity in SNvin reactions, polyhalo-nitro-butadienes have been shown in many studies to have many properties as well as medical and pharmaceutical effects such as antitumor, bactericidal, fungicide and algicide. This study deals with the design, characterization of structures and the discovery of their antibacterial and antifungal properties based on new (E)-S- and (E)-N,S-polyhalonitrobutadiene analogues possessing piperazine, piperidine and morpholine groups. The antibacterial and antifungal activity of synthesized S- and N,S-substituted perhalo-nitro-butadienes were evaluated against to Escherichia coli B-906, Staphylococcus aureus 209-P, Mycobacterium luteum B-917 for bacteria and Candida tenuis VKM Y-70, Aspergillus niger F-1119 for fungi. Antimicrobial activity of the synthesized compounds was determined by using the diffusion method and serial dilution method. Compounds 2-Nitro-1,3,4,4-tetrachloro-1-hexylsulfanyl-1,3-butadiene and (E)-2,6-dimethyl-4-(3,4,4-trichloro-2-nitro-1-(octylthio)buta-1,3-dien-1-yl)morpholine with high antibacterial effect against strains E. coli and M. luteum and the derivative (E)-1-benzhydryl-4-(3,4,4-trichloro-1-(hexylthio)-2-nitrobuta-1,3-dien-1-yl)piperazine with antifungal agent against test-cultures A. niger and C. tenuis at MIC 1.9 µg/mL were identified as the most potent. Synopsis This study deals with the characterization of structures and the discovery of their antibacterial and antifungal properties based on new (E)-N,S-polyhalonitrobutadiene analogues. 1b and 7 with high antibacterial effect against strains E. coli and M. luteum. 9 with antifungal agent against test-cultures A. niger, C. tenuis at MIC 1.9 µg/mL were identified as the most potent.

Досліджено протон-ініційоване перетво- рення дитіокарбаматних похідних 9,10-антрацендіону за умов кислотно-каталізованої циклодегідратації при дії суміші H2SO4-АсОН та подальшому обробленні перхлоратною кислотою. На основі даних спектральних методів (1Н, 13С ЯМР, ІЧ-, УФ-спектроскопії) встановлено, що реакція зупи- няється на стадії протонування атома Сульфуру тіокар- бонільної групи з утворенням перхлоратних солей. УФ спектри одержаних перхлоратів характеризуються гіпсохромним зсувом з чітко вираженим максимумом поглинання. Proton-initiated conversion of dithiocarbamate derivatives of the 9,10-anthracenedione under conditions of acid-catalyzed cyclodehydration using the action of a mixture of H2SO4-AcOH and further treatment with perchloric acid was investigated. Based on the data of the spectral methods (1H, 13C NMR, IR, UV spectroscopy), it is established that the reaction stops at the stage of protonation of the sulfur atom of the thiocarbonyl group with the formation of perchlorates. The UV spectra of the obtained perchlorates are characterized by a hypochromic shift with a clearly pronounced absorption maximum.

The new anthraquinonylhydrazones were obtained by the interaction of 9,10-dioxoanthracene-1-diazonium sulfates with a number of α- and β-carbonyl-containing compounds under modified conditions of the Japp–Klingemann reaction, and a probable mechanism of the formation has been proposed. It was found that hydrazones, unsaturated in the second position of the anthraquinone ring, containing acetyl or ethoxycarbonyl moieties in the ylidene part of the molecule, are capable of eliminating these fragments. It has been experimentally established that hydrazones, free rotation around the N=C bond of which is possible, exist as one isomer due to the presence of an intramolecular hydrogen bond in the molecule. The anthraquinonylhydrazone of dimedone with action against the bacteria strains of Staphylococcus aureus 209-P, Mycobacterium luteum B-917, and fungus Candida tenuis VKM Y-70 was found. The hydrazones of dimedone and barbituric acid with a higher trolox equivalent antioxidant coefficients of antioxidant action were found using CUPRAC assay. In addition, the hydrazones of dimedone and barbituric acid exhibited better activity against catalase enzyme. Correlations between the structure of the synthesized hydrazones and their antioxidant activity have been defined.

Anticancer activity as an associated action for a series of dithiocarbamates of 9,10-anthracenedione was predicted using the PASS computer program and analysed with PharmaExpert software. The predicted cytotoxic activity of the dithiocarbamate derivatives of 9,10-anthracenedione was evaluated in vitro on cancer cells of the human lung (A549), prostate (PC3), colon (HT29) and human breast (MCF7) using the sulforhodamine B (SRB) cell viability assay. Among these compounds, 9,10-dioxo-9,10-dihydroanthracen-1-yl pyrrolidin-1-carbodithioate and 9,10-dioxo-9,10-dihydroanthracen-2-yl pyrrolidin-1-carbodithioate were identified as the most potent anticancer agents with cytotoxic activity against the MCF-7 human breast cell line with GI(50) values of 1.40 M and 1.52 M, whereas the GI(50) value for the reference anticancer drug mitoxantrone was 3.93 M. Thus, anticancer activity predicted by PASS with a probability Pa > 30% was confirmed by the experiment. Relatively small Pa values estimated by PASS indicated the novelty of the considered derivatives comparing to the compounds from the PASS training set. Ministry of Education and Science of Ukraine, Scientific Research Project [0116U004138]; Scientific Research Projects Coordination Unit of Istanbul UniversityIstanbul University [NP-45621]; Russian State Academies of Sciences Fundamental Research Program The authors would like to express their gratitude to the Ministry of Education and Science of Ukraine, Scientific Research Project (Project Number: 0116U004138), Scientific Research Projects Coordination Unit of Istanbul University (Project Number: NP-45621) and to the Russian State Academies of Sciences Fundamental Research Program for 2013-2020 (VP and TG) for financial support. WOS:000402994100001 28524703 Q1

Досліджено реакції 1,4(1,5)-діазидо-9,10- антрацендіонів із фенілацетиленом та метиловим естером ацетиленкарбонової кислоти за умов купрум(І)-каталізованої реакції азид-алкінового циклоприєднання та одержано ряд нових 1,2,3-триазолільних похідних 9,10-антрацендіону. Для визначення напрямків експериментальних біомедичних досліджень синтезованих сполук проведено комп’ютерний скринінг програмою PASS Online. Молекулярний докінг нових синтезованих 1,2,3-триазолів 9,10-антрацендіону виявив спо- луки з високим ступенем афінітету до сімейства рецепторних тирозинкіназ епідермального фактору росту EGFR, що може свідчити про ймовірний механізм реалізації протипухлинної активності.

The nitro group–substituted perhalogenobuta-1,3-diene (1) is important synthetic precursor in the synthesis of different heterocycles groups with high biological activity. Firstly, new N,S-substituted-perhalonitro-1,3-butadiene compounds were synthesized by the reactions of various amino or thiol containing nucleophiles with 1. The structures of all new compounds have been identified by using spectroscopic techniques (FT-IR, 1H-NMR, 13C-NMR, MS and microanalysis). Secondly, their antimicrobial properties were tested as potential antibacterial and antifungal agents. Antimicrobial activity of synthesized N,S-substituted perhalonitrobutadienes 4a–j and 5a–d was evaluated against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi and the compounds 4c, 4d, 5a and 5b with high antifungal action against test-culture Aspergillus niger at MIC values 0.9–1.9 μg/cm3 were identified as the most potent.

9,10-Dioxoanthracenyl-1(2)-diazonium hydrosulfates reacted with pyridine under both the modified Gomberg–Bachmann reaction conditions and in the presence of catalytic amounts of CuCl2 to form a mixture of isomeric 2-, 3-, and 4-pyridylanthraquinones, of which 2-pyridyl derivatives were isolated in an analytically pure form.

A variety of new derivatives of 9,10-anthracenedione with mono- and bisdithiocarbamate moiety in the non-catalytic conditions have been synthesized. The obtained compounds were screened for their antioxidant capacity using the cupric-reducing antioxidant capacity (CUPRAC) method. Three of the compounds showed CUPRAC-Trolox equivalent antioxidant capacity (TEAC) coefficients higher than trolox. Scavenging effects on reactive oxygen species (ROS), hydroxyl radical scavenging (HRS), hydrogen peroxide scavenging (HPS), and superoxide anion radical scavenging (SARS) of all synthesized compounds were determined. It was established that the results of HRS-, HPS-, and SARS-CUPRAC methods for three compounds are in accordance with TEAC-CUPRAC assay data.

9,10-Anthraquinonylhydrazones containing nitrile, acyl, and ethoxycarbonyl groups reacted with hydrazine hydrate upon refluxing in dioxane or with sodium azide upon heating in DMF, giving the corresponding pyrazole and tetrazole derivatives.

Derivatives of 2(5 H)-furanone (γ-crotonolactone) are important intermediate synthetic products with a wide range of biological effects that have become widely used in the pharmaceutical industry, medicine, and veterinary medicine, in particular in the prevention and treatment of fish diseases. However, the environmental issue of obtaining these compounds while reducing the negative impact on the surrounding environment remains relevant. This article describes for the first time a method of γ-crotonolactone synthesis that is based on the concept of green chemistry. Synthesis is carried out under mild conditions using nontoxic reagents by furfural oxidation. For the first time, a mixture of hydrogen peroxide and acetic acid was used for the oxidation of furfural in a ratio of 1:0.05. A mixture of organic acids (succinic, maleic, fumaric, formic, and cinnamic acids), obtained as a byproduct in the synthesis of γ-crotonolactone, can be used as a highly effective, ecofriendly organic fertilizer or in a preparation with a stimulating effect.

Взаємодією (9,10-діоксоантраценіл-1)-гідразонів малонодинітрилу, етилових естерів ціанацетатної та ацетацетатної кислот, а також ацетилацетону із гідроксил аміном у киплячому діоксані у присутності ацетату натрію проведено модифікацію функціоналізованого гідразонного угруповання амідоксимними фрагментами. Встановлено, що реакція N-(9,10-діоксо-9,10-дигідроантрацен-1-іл)карбоногід-разоноілдиціаніду 1 з NH2OH приводить до утворення 2-(2-(9,10-діоксо-9,10-дигідроантрацен-1-іл)гідразиніліден)-N'1,N'3-дигідроксималонімідаміду 2 як основного та 3-аміно-2-(2-(9,10-діоксо-9,10-дигідроантрацен-1-іл)гідразиніліден)-3-(гідрокси-іміно)пропанаміду 3 як мінорного продукта. Методами 1Н, 13С ЯМР-спектроскопії та хроматомас-спектрометрії встановлено, що взаємодія 9,10-діоксоантраценілгідразону ацетил ацетону 5 із гідроксиламіном супроводжується елімінуванням ацетильного фрагмента, наслідком чого є утворення 1-[2-(2-(гідроксиіміно)пропіліден)гідразиніл]антрацен-9,10-діону 9. Запропоновано вірогідні механізми утворення амідоксимів 3 та 9. Проведені квантово-хімічні DFT-розрахунки вільної енергії ГіббсаDG для амідоксимної форми похідних 2, 3, 7-9 гібридним методом М06-2Х в базисному наборі 6-311++G(d,p) із використанням сольватаційної моделі SMD у ДМСО з метою визначення конформаційної переваги Z- або E-ізомерів. New (9,10-dioxoanthracen-1-yl)hydrazones containing amidoxime fragments were synthesized by the interaction of corresponding hydrazones of malonodinitrile, ethyl cyanacetate, ethyl acetoacetate, and acetylacetone with hydroxylamine in boiling dioxane in the presence of sodium acetate. It was established that the reaction of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)carbonohydrazonoyldicyanide 1 with NH2OH leads to the formation of 2-(2-(9,10-dioxo-9,10-dihydroanthracen-1-yl)hydrazinylidene)-N'1,N'3-dihydroxymalonimidamide 2 as the major product, and 3-amino-2-(2-(9,10-dioxo-9,10-dihydroanthracen-1-yl)hydrazinylidene)-3-(hydroxyimino) propanamide 3 as a minor product. The 1H, 13C NMR and LC-MS data showed that the interaction of 9,10-dioxoanthracenylhydrazone of acetylacetone 5 by hydroxylamine is accompanied with the elimination of the acetyl fragment formed 1-[2-(2-(hydroxyimino) propylidene)hydrazinyl]anthracene-9,10-dione 9. Possible mechanisms for the formation of amidoximes 3 and 9 are proposed. Quantum-chemical DFT calculations of the Gibbs free energy (DG) to determine conformational advantage of Z- or E-isomers for the amidoxime form of the derivatives 2,3,7-9 were carried out using the M06-2X hybrid method with 6-311++G(d, p) basis set and the SMD solvation model in DMSO.

Novel functionalized thiazoles were prepared by the Hantzsch reaction from 3-[(4-hydroxyphenyl)carbamothioylamino]-2-methylpropanoic acid and the corresponding α-halocarbonyl compounds in good yields. A series of chemical transformations of the obtained products were carried out, and new functionalized thiazole derivatives with aliphatic, aromatic and heterocyclic substituents were synthesized. 4-Phenyl-substituted N-(4-hydroxyphenyl)-N-carboxyalkylaminothiazoles were used as precursors for the synthesis of bis(thiazol-5-yl)methane derivatives, which then were screened for their antibacterial, antioxidant activities.

The significance of the acylation reaction of amines is presented in the literary reference information. The products of the reaction of the corresponding amides are important intermediates in obtaining practically useful compounds. It has been shown that the most common methods of acylfunctionalization of amines are acetylation, trifluoroacetylation and formylation, usually acid anhydrides or chlorides are used as acylating reagents in these reactions in the presence of highly toxic and expensive catalysts. The authors have developed an approach to the synthesis of a number of N-acylated amino-9,10-anthraquinones, which is based on the use of a new acylation system consisting of a strong organic acid and ammonium thiocyanate. It has been determined that 1-amino-9,10-anthraquinone and its derivatives in the presence of the two-fold excess of ammonium thiocyanate can be acetylated only by formic and trifluoroacetic acids. 2-Amino-9,10-anthraquinone additionally can be acetylated by mercaptoacetic and acetic acids. The scheme of the reaction discovered has been proposed, it involves in situ generation of ammonium acetate from carboxylic acid and ammonium thiocyanate, which serves as the acylating reagent.

A method for the preparation of (1H-pyrrol-1-yl)anthracene-9,10-diones under the conditions of an iodine-catalyzed Clauson–Kaas reaction is proposed.

The influence of new derivatives of 9,10-anthraquinone with benzoylthiourea, thiazole, triazole and amino acid fragments on the activity of membrane-associated tyrosine kinases was investigated. Inhibitors of protein tyrosine kinase activity of the membrane fraction, as promising agents to search for new potential anticancer agents among the studied compounds, were discovered.

The development and spread of resistance of human pathogenic bacteria to the action of commonly used antibacterial drugs is one of the key problems in modern medicine. One of the especially dangerous and easily developing antibiotic resistant bacterial species is Staphylococcus aureus. Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones 22&ndash, 38 have been developed as novel effective antistaphylococcal agents. These compounds have been obtained by sequential conversion of 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (1) and 1-amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (2) into the corresponding amides 5&ndash, 21, followed by subsequent endo-cyclization under the influence of sodium nitrite in acetic acid. Evaluation of the antimicrobial activity of the synthesized compounds against selected species of Gram-positive and Gram-negative bacteria as well as pathogenic yeasts of the Candida genus has been carried out by the serial dilution method. It has been established that anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones exhibit selective antibacterial activity against Gram-positive bacteria. Eight, six and seven, out of seventeen compounds tested, effectively inhibited the growth of S. aureus ATCC 25923, S. aureus ATCC 29213 and S. epidermidis ATCC12228, respectively, at a concentration equal to 1 &micro, g/mL or lower. The high antistaphylococcal potential of the most active compounds has been also confirmed against clinical isolates of S. aureus, including the MRSA strains. However, bacteria of the Staphylococcus genus have demonstrated apparent resistance to the novel compounds when grown as a biofilm. None of the four selected compounds 3234 and 36 at a concentration of 64 &micro, g/mL (128 or 256 &times, MIC&mdash, against planktonic cells) has caused any decrease in the metabolic activity of the staphylococcal cells forming the biofilm. The kinetic time&ndash, kill assay revealed some important differences in the activity of these substances. Compound 33 is bacteriostatic, while the other three demonstrate bactericidal activity.

The title compounds are prepared from (amino)anthracenediones and (dimethoxy)tetrahydrofuran via Clauson—Kaas reaction using I2 as catalyst.

An efficient procedure has been proposed for the synthesis of previously unknown 1-hydrazinylanthraquinones containing acyl and/or ester fragments convenient for subsequent transformations.

N-Aroylthioureas hold a significant promise for the synthesis of such heterocycles as imidazolidine2-thiones [1, 2], 2-aroyliminothiazolines [3-5], 1,2,4-triazoles [6], 1,3-thiazines [7], and indeno[1,2-d][1,3]thiazepines [8]. Of particular interest are 2-iminothiazolines, which are characterized by a wide range of biological properties [9-11]. For example, the thiazol-2-imine fragment is a structural fragment in muscarinic agonists, as well as antifungal, hypolipidemic, antidiabetic, anti-inflammatory, analgesic, and anti-shistosomiasis compounds [5]. Thiazoline derivatives are also used as insecticides and plant growth regulators [5]. The reaction of N,N'-disubstituted thioureas with α-bromo ketones has been described in the literature [5, 12], and it provides access to various N-substituted 2-iminothiazoles. However, 2-iminothiazoles with 9,10-dioxo9,10-dihydroanthracenyl substituents at position 3 of the heterocycle remain hitherto unknown. The pronounced biological properties of anthraquinone derivatives [13-15] motivate the search for hybrid structures that include both anthraquinone and thiazole ring systems. Based on these considerations, we treated our previously described N-benzoyl-N'-(9,10-dioxo9,10-dihydroanthracen-1-yl)thioureas 1а-е [16] with in situ generated α-bromoacetone in the presence of triethylamine and obtained the 2-(N-benzoylimino)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)thiazoles 2а-е in 48-68% yields. The formation of 2-(N-benzoyl)imine type thiazoles through a cyclocondensation with the participation of aminoanthracene nitrogen atom was in agreement with the recently described reactions of N-arylN'-aroylthioureas with α-halo ketones [4, 12, 13]. The Н NMR spectra of the compounds 2а-е contained thiazole H-5 proton singlets at 6.89-7.01 ppm and methyl group singlets at 1.97-2.04 ppm, besides the CH signals of the aromatic rings. The formation of a thiazole ring was also clearly confirmed by the С spectra containing the characteristic С-4 singlets at 106.1-107.2 ppm, С-5 singlets at 139.3-144.9 ppm, and С-2 singlets at 168.2-169.7 ppm. The C signals of the thiazole 4-СН3 substituent were found at 13.7-14.2 ppm, which was typical for 3-aryl-2-benzoylimino-4-methyl-1,3-thiazolines [4, 5]. Thus, we have prepared new 2-(N-benzoylimino)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)thiazoles by a novel route, starting from N-benzoyl-N'-(9,10-dioxo-9,10-dihydroanthracen-1-yl)thioureas.

New thiazole and 1,2,4-triazole derivatives of 9,10-anthraquinone were obtained by the reaction of N-benzoyl-N'-(9,10-dioxo-9,10-dihydroanthracene-1-yl)-thioureas with bromoacetone in the presence of triethylamine and hydrazine hydrate in chloroform, respectively. The PASS computer program was used to predict the biological activity spectra and to determine the most promising biological activities for experimental testing. Thus, it has been shown that the synthesized compounds are a promising class for the creation of substances with a wide range of biological activity. DOI: http://dx.doi.org/10.5755/j01.ct.64.2.6018

Notwithstanding the well studied 9,10-anthraquinone chemistry many its derivatives are poorly understood up till now. Among them are, in particular, the derivatives of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide (I) [1–5]. We carried out reactions of compound I with various amino acids: glycine, alanine, phenylalanine, valine, leucine, and methionine IIa–IIf in the presence of potassium carbonate in DMSO at heating. Target products IIIa–IIIf were isolated from the reaction mixture diluting the latter with 5-fold volume of water followed by acidifying with dilute hydrochloric acid. The separated solid precipitate was fi ltered off and purifi ed by recrystallization from a mixture acetonitrile– water, 1 : 5. {2-[(9,10-Dioxy-9,10-dihydroanthracen-1-yl)amino]-2-oxoethyl}glycine (IIIa). Yield 54%, mp 196°С. IR spectrum, ν, cm–1: 3425 (CH2NH), 3345 (NHСО), 3000–2500 (COОН), 1720 (С=О in COOH), 1680, 1631 (С=О quinoid ring), 1645 (СОNH). 1Н NMR spectrum, δ, ppm: 12.66 s (1H, OH), 10.72 s (1H, NH), 8.94 d (1Harom, J 7.7 Hz), 8.14–8.21 m (3Harom), 7.91 m

Interaction of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide with α-, β- and ω-amino acids was used to synthesize new amino-acid derivatives of 9,10-anthraquinone. Experimental testing of the antimicrobial actions of the compounds synthesized demonstrated antibacterial activity against Mycobacterium luteum and antifungal activity against Aspergillus niger and Candida tenuis. These results from experimental testing of biological activity are consistent with results obtained by predictions using the computer program PASS. The prediction identified the need for further study of the antitumor and antioxidant actions of the newly synthesized amino acid derivatives.