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1.

3-Formylpyrazolo[1,5-a]pyrazine-4-carboxylates as new bielectrophilic reagents in the cascade synthesis of polyazaacenaphthylene and polyazaacetanthrylene derivatives Pages 399-406 Right click to download the paper Download PDF

Authors: Nazar Tsyzoryk, Khrystyna Loza, Andriy Bolbut, Svitlana Shishkina, Maryna Stasevych, Mykhailo Vovk

DOI: 10.5267/j.ccl.2025.5.002

Keywords: Pyrazolo[1, 5-a]pyrazine-4-carboxylates, 3-formylpyrazolo[1, 5-a]pyrazine-4-carboxylates, 1, 5-bielectrophilic reagents, Diaminoalkanes, Cascade reactions, Pentaazacyclopenta[d]acenaphthalenes, Pentaazaaceanthrylenes

Abstract:
It has been shown that 3-formylpyrazolo[1,5-a]pyrazine-4-carboxylates obtained by the selective formylation of pyrazolo[1,5-a]pyrazine-4-carboxylates react with 1,2-ethanediamine or 1,3-propanediamine in methanol at room temperature to give pentaazacyclopenta[d]acenaphthalenes or pentaazaaceanthrylenes.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 3 | Views: 54 | Reviews: 0

 
2.

Synthesis of pyrrolo(pyrido)[1,2-a]quinazolinones and their benzoannulated analogues: An overview Pages 507-532 Right click to download the paper Download PDF

Authors: Alla Vaskevych, Nataliia Savinchuk, Mykhailo Vov

DOI: 10.5267/j.ccl.2025.3.005

Keywords: Alkaloids, Quinazoline-4(3H)-ones, Pyrrolo(pyrido)[1, 2-a]quinazolinones, Cyclocondensation, Annulation

Abstract:
Angular pyrrolo(pyrido)[1,2-a]quinazolinones, being structurally isomeric to linear pyrrolo(pyrido)[2,1-b]quinazolinone alkaloids, are attractive molecular systems for both synthetic transformations and targeted biomedical research. The pyrrolo(pyrido)[1,2-a]quinazolinone scaffold has proven to be quite effective in the search for compounds with a wide range of pharmacological activities, e.g. anti-inflammatory, antioxidant, antibacterial, antiarrhythmic, and inhibitors of important biotargets. The present review summarises the methods for the synthesis of pyrrolo(pyrido)[1,2-a]quinazolinones as a comprehensive research object, especially in the past decade. They are systematised according to the type of heteroannulation and include the processes of cascade annulation of the pyrimidine and pyrrole (pyridine) cycles to anthranilamides (hydrazides); formation of a pyrimidine nucleus based on ortho-pyrrolyl(pyridinyl) substituted aromatic compounds; annulation of the pyrrole (pyridine) nucleus to a quinazolinone scaffold. It is expected that the generalised material presented will serve as a reliable guide for the rational design of new pharmacologically oriented compounds.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 3 | Views: 58 | Reviews: 0

 
3.

Synthesis and thermodynamic properties of 3-(5-phenyl-1-(pyridin-3-yl)-1H-pyrrol-2-yl)propanoic acid in condensed and gaseous states Pages 559-566 Right click to download the paper Download PDF

Authors: Dmytro Shevchenko, Yuriy Horak, Mykola Obushak, Nadiia Tischenko, Iryna Sobechko

DOI: 10.5267/j.ccl.2025.3.002

Keywords: Enthalpy of formation, Enthalpies of phase transitions, Analytical calculations, Pyrrole derivatives, N-substituted 3-(5-phenylpyrrol-2-yl)propanoic acids

Abstract:
A combined experimental and theoretical study of the fundamental thermodynamic parameters of 3-(5-phenyl-1-(pyridin-3-yl)-1H-pyrrol-2-yl)propanoic acid was carried out for the first time. The enthalpies of combustion, formation in the condensed state, fusion, and vaporization were determined using high-precision equipment. Based on the experimentally obtained results, the enthalpies of sublimation and formation in the gaseous state at 298.15 K were calculated using two methods. The possibility of applying analytical methods of Domalski, Joback and quantum chemical calculations to determine the enthalpy of formation in the gas phase is analysed.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 3 | Views: 86 | Reviews: 0

 
4.

Pharmacological profile of condensed heterocyclic compounds based on functionally substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles: A review Pages 567-578 Right click to download the paper Download PDF

Authors: Maryan Lelyukh, Arkady Savchenko, Myroslava Kalytovska, Maria Zhukrovska, Ihor Chaban, Andrii Vergun, Lesya Shelepeten, Taras Chaban

DOI: 10.5267/j.ccl.2025.3.001

Keywords: Heterocyclic compounds, Triazolo[3, 4b][1, 3, 4]thiadiazoles, Pharmacological activity

Abstract:
Triazolo[3,4-b][1,3,4]thiadiazole molecules are found to be important tools in modern bioorganic and medicinal chemistry. This condensed system successfully combines two pharmacologically significant five-membered heterocycles – 1,2,4-triazole and 1,3,4-thiadiazole, which causes much more interest in the enhanced activity profile of its analogs than their parent separate constituents. It’s considered that the triazoles fused to thiadiazoles exhibit various therapeutically important properties, probably due to the existence of N-C-S fragments in their structures. In this review, we presented the summarized literature data about the diversity of pharmacological effects of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole based compounds as promising objects for the rational design of drug-like molecules.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 3 | Views: 30 | Reviews: 0

 
5.

Antioxidant activity, DFT-calculation, and docking of 5-amino-N-(3-di(per)fluoroalkyl-2-iodo-n-propyl)-1,2,3-triazole-4-carboxamides Pages 251-264 Right click to download the paper Download PDF

Authors: Ivanna Danyliuk, Sergiy Kemskyi, Lesya Saliyeva, Nataliia Slyvka, Dmytro Melnyk, Oksana Melnyk, Victor Dorokhov, Mykhailo Vovk

DOI: 10.5267/j.ccl.2024.12.002

Keywords: Iododi(per)fluoroalkylation, DPPH, Antioxidant activity, Docking studies

Abstract:
Antioxidant activity of a series of previously described 5-amino-N-(iododi(per)fluoroalkyl)-1H-1,2,3-triazole-4-carboxamides 3a-r, their synthetic precursors 5-amino-N-allyl-1,2,3-triazole-4-carboxamides 1a-g, and their deamination products N-(3-di(per)fluoroalkyl-2-iodo-n-propyl)-1,2,3-triazole-4-carboxamides 4a-e was investigated in vitro using DPPH test and ascorbic acid as a standard reference. It was established that compounds 3a-r inhibit DPPH free radicals in moderate to high values (50.9–97.6%). The effect of substituents in the position 1 of the 1,2,3-triazole nucleus, fluoroalkyl groups and amino groups on the level of antioxidant activity was studied in detail. Reactivity and electrostatic surface potential were evaluated for the most active carboxamides 3a,g,r using the DFT method, and molecular docking was studied in the NADPH oxidase protein model.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 2 | Views: 283 | Reviews: 0

 
6.

In vitro evaluation of antibacterial and antibiofilm activity of new bis-quaternary ammonium compounds based on natural products Pages 271-278 Right click to download the paper Download PDF

Authors: Liubov Muzychka, Diana Hodyna, Larysa Metelytsia, Oleg Smolii

DOI: 10.5267/j.ccl.2024.11.007

Keywords: Bis-quaternary ammonium compounds, Natural products, Antibiofilm, Antibacterial activity

Abstract:
Continuing the search for new antimicrobial agents with antibiofilm activity, bis-quaternary ammonium compounds based on natural (3,5-dibromo-4-hydroxyphenyl)acetic acid derivatives were synthesized. Antibacterial and antibiofilm activity of ammonium salts was evaluated in vitro against S. aureus, E. coli, and P. aeruginosa, including antibiotic-resistant strains. Bis-quaternary ammonium salts 1, 5, and 6 showed antibacterial activity with MIC values ranging from 25.0 to 200.0 μg/mL. Notably, these compounds demonstrated a high level of antibiofilm activity. Ammonium salts 1 and 6 reduced biofilm formation against S. aureus ATCC 25923, P. aeruginosa PA01, E. coli ATCC 25922, and antibiotic-resistant P. aeruginosa by 92 - 97% at a concentration of 100.0 μg/mL. In addition, compounds 1 and 6 inhibited the biofilm formation of antibiotic-resistant E. coli isolate by 60% and 63%, respectively.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 2 | Views: 187 | Reviews: 0

 
7.

Antioxidant properties of some 4-arylimino-thiazolidin-2-ones Pages 365-372 Right click to download the paper Download PDF

Authors: Zoriana Сhulovska, Taras Chaban, Arkady Savchenko, Olexandra Komarytsya, Marta Dasho, Maryan Lelyukh, Ihor Chaban, Volodymyr Ogurtso

DOI: 10.5267/j.ccl.2024.11.001

Keywords: Synthesis, 4-Arylimino-thiazolidin-2-ones, DPPH, Antioxidant activity

Abstract:
In the present work, we report an efficient synthesis and antioxidant activity evaluation of some 4-arylimino-thiazolidin-2-ones. The structures of target substances were confirmed through 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The antioxidant activity of the synthesized compounds was measured in vitro by the method of scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals. Notably, antioxidant activity was identified for the first time among 4-arylimino-thiazolidin-2-ones.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 2 | Views: 232 | Reviews: 0

 
8.

Synthesis and some chemical transformations of novel 1-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acids and their benzoannelated analogues Pages 69-78 Right click to download the paper Download PDF

Authors: Mariia Litvinchuk, Anton Bentya, Svitlana Shishkina, Mykhailo Vov

DOI: 10.5267/j.ccl.2024.9.004

Keywords: Methyl (2-oxo-2H-(benz)oxazine-3(4H)-ylidene)ethanoates, 2-Bromo-1, 1-diethoxyethane, Pyrrolo[2, 1-c][1, 4](benz)oxazinecarboxylic acids, Amino-1H-pyrrolo[2, 1-c][1, 4](benz)oxazinones, Carbox(sulfone)amides

Abstract:
A preparatively convenient method is proposed for the synthesis of new 1-oxo-3,4-dihydro-1H-pyrrolo[2,1-с][1,4]oxazine-8- 4a-e and 4-oxo-4H-pyrrolo[2,1-c][1,4]benzoxazine-3-carboxylic acids 5a-f that is based on the interaction of methyl (2-oxomorpholin-3-ylidene)ethanoates 1a-e and methyl (2-oxo-2H-1,4-benzoxazine-3(4H)-ylidene)ethanoates 2a-f with 2-bromo-1,1-diethoxyethane. Obtained acids were transformed into the corresponding tert-butyl carbamates 6a-e, 7a-f and N-alkyl(aryl)carboxamides 11a-i, 12a-d. By treating tert-butyl carbamates 6a-e, 7a-f with hydrogen chloride, 8-amino-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazin-1-ones 8a-e and 3-amino-4H-pyrrolo[2,1-c][1,4]benzoxazin-4-ones 9a-f were obtained. By acylation of amines 8a-e, 9a-f with acetic anhydride, benzoyl chloride, methanesulfonyl chloride, and p-toluenesulfonyl chloride, corresponding N-acetamides 13a,b, 14, N-benzamides 15, 16, N-methanesulfonamides 17, 18, and N-p-toluenesulfonamides 19, 20 were synthesized. In total, 30 new derivatives of 1-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazinones and 27 new 4-oxo-4H-pyrrolo[2,1-c][1,4]benzoxazinones were obtained.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 1 | Views: 695 | Reviews: 0

 
9.

Synthesis, antimicrobial and antioxidant activity evaluation, DFT-calculation, and docking studies of 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles Pages 107-118 Right click to download the paper Download PDF

Authors: Vasyl Zhylko, Lesya Saliyeva, Nataliia Slyvka, Alina Grozav, Nina Yakovychuk, Dmytro Melnyk, Oksana Melnyk, Mariia Litvinchuk, Mykhailo Vov

DOI: 10.5267/j.ccl.2024.9.002

Keywords: Imidazo[2, 1-b]thiazole, Cyclocondensation, Antimicrobial activity, Antioxidant activity, Docking studies

Abstract:
A number of 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles were synthesized by cyclocondensation of imidazolidine-2-thione with phenacyl bromides, and their antimicrobial and antioxidant activity was evaluated. Bioscreening confirmed the moderate antibacterial activity against the reference strains of bacteria Staphylococcus aureus, Escherichia coli and Proteus vulgaris and excellent antifungal activity against Candida albicans. It was found that 3-(4-chlorophenyl)-5,6-dihydroimidazo[2,1-b]thiazole 4h (MIC = 15.625 μg/ml) has twice the antifungal effect compared to the control drug Furacilin. The study of the antioxidant activity of the synthesized compounds proved their ability to inhibit 60–97% of DPPH radicals. The best antiradical effect was found for 4-(5,6-dihydroimidazo[2,1-b]thiazol-3-yl)phenol 4e (I = 97%). A probable mechanism of its action was proposed involving the formation of a radical cation by the SET process. For the most active antioxidants 4e-g, reactivity and electrostatic surface potential were evaluated using the DFT method, and molecular docking was studied on the human peroxiredoxin 5 protein model.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 1 | Views: 328 | Reviews: 0

 
10.

Synthesis and antitumor activity of 2-cyanocinnamic acid amides and their indole analogues Pages 119-128 Right click to download the paper Download PDF

Authors: Yuliia Matiichuk, Iryna Drapak, Serhii Kramarenko, Yana Drapak, Liybov Kostyshyn, Nataliya Shtoyko, Vasyl Matiychuk

DOI: 10.5267/j.ccl.2024.9.001

Keywords: Acrylonitrile, Thiazole, Indole, Knoevenagel reaction, Anticancer Activity

Abstract:
By the reaction of substituted benzaldehydes and indol-3-carbaldehydes (2E)-2-cyano-N-[5-(R-benzyl)-1,3-thiazol-2-yl]-3-(R1-phenyl)prop-2-enamides 3-(1-R1-1H-indol-3-yl)-2-cyano-N-(5-(R-benzyl)-1,3-thiazol-2-yl)prop-2-enamides were synthesised. The antitumor activity of prepared compounds were investigated. 3-(1-Benzyl-1H-indol-3-yl)-2-cyano-N-(5-(2-chlorobenzyl)-1,3-thiazol-2-yl)prop-2-enamide (7b) has been identified as hit compound with values of MG-MID GI50 = 3.903 µM, TGI = 29.10 µM, LC50 = 57.54 µM.
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Journal: CCL | Year: 2025 | Volume: 14 | Issue: 1 | Views: 331 | Reviews: 0

 
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