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Registration Number

0225U004568, (0120U104977) , R & D reports

Title

Functional design, synthesis and directed modification of bioattractive condensed azole, azine and azepine compounds

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Функціональний дизайн, синтез та спрямована модифікація біопривабливих конденсованих азольних, азинових та азепінових сполук

Head

Vovk Mykhailo V., Доктор хімічних наук

Registration Date

11-12-2025

Organization

Institute of Organic Chemistry NAS of Ukraine

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The purpose of the work is to create methodological bases for designing new promising for organic synthesis and biomedical research types of azole-azole (pyrrolothiazoles, imidazothiazoles), azole-azine (pyrazolopyridines, pyrazolopyrimidines, pyrazolopyrazines, 1,2,3-triazolopyridines, 1,2,3-triazolopyrimidines, pyrroloquinazolines) and azolo-azepine (pyrazoloazepines, 1,2,3-triazoloazepines) compounds, structurally modified by linear-functional and heteroanelated fragments. In this case, considerable attention will be focused on the design of those condensed derivatives that contain key for further synthetic transformations haloalkyl, formyl, carboxyl, alkenyl, alkynyl, amino and hydrazino groups. To achieve this goal, the known and new, especially catalytic, methods of functionalization and annelation of small and medium heterocyclic nuclei to basic azole and azine templates will be significantly improved and developed. An important role in the research process will be assigned to the establishment of patterns of regio- and stereocontrol in the implementation of highly selective cyclization methods for the directed synthesis of condensed heterocyclic compounds as molecular platforms for the design of bioactive substances. The pronounced pharmacological properties of functional derivatives of heteroanylelated azoles, azines and azepines seem to be an important basis both for the development of effective synthetic approaches to their new representatives and for selective modification to obtain compounds with a wide segment of biological action.

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The project is aimed at creating methodological foundations of constructing new types of azole-azoles (pyrrolothiazoles, imidazothiazoles), azolo-azine (pyrazolopyridines, pyrazolopyrimidines, pyrazolopyrazines, 1,2,3-triazolopyridines, 1,2,3-triazolopyrimidines, pyrroloquinazolines) and azolo-azepine (pyrazoloazepines, 1,2,3-triazoloazepines) compounds, structurally modified by linear functional and heteroanullated fragments. In this case, considerable attention was paid to the design of those condensed derivatives that contain halogenoalkyl, formyl, carboxyl, alkenyl, alkynyl, amino and hydrazine groups, which are crucial for further synthetic transformations. The selective methods were developed for obtaining analogues of quinazoline alkaloids – linear and angular dihydropyrolo(pyrid)quinazolinones, based on intramolecular cyclisation of 2-alkenylquinazolin-4(3H)-ones under the action of electrophilic and radical initiators using the newest synthesis methodologies. An innovative method of direct regioselective organophotocatalytic aminomethylation of pyrimidine-2(1H)-ones with N-Boc aminoalkyltrifluoroborates has been found. Series of n,π-chelate complexes of Palladium and Platinum with N-allylthiourea derivatives were obtained, which are structural analogous to the well-known antitumour drug ‘Cisplatin’. To achieve this goal, known methods were significantly improved and new, primarily catalytic, eco-friendly photo-initiated methods for the functionalisation and annulation of small and medium-sized heterocyclic rings to basic azole and azine templates were developed. An important role in the research process was dedicated to establishing the regularities of regio- and stereocontrol in the implementation of highly selective cyclisation methods for the targeted synthesis of condensed heterocyclic compounds as frameworks for the design of bioactive substances. Evaluation of the various biological effects of the synthesized new chemical substances was carried out.

Product Description

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Kemskii Serhii V.
Loza Kristina Olegivna
Tsyzoryk Nazar Mykhailovych
Anton V. Bentya
Orysyk Viktor V.
Litvinchuk Mariia B
Bol'but Andriy V.
Vas'kevych Ruslan I.
Zborovskii Yuriy L.
Tkachuk Viktor
Oleh Lukianov
Alla I. Vaskevych
Ivanna Y. Danyliuk

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2025-12-11