: 47-53
Lviv Polytechnic National University
National University Lviv Polytechnic
Lviv Polytechnic National University
Lviv Polytechnic National University
Lviv Polytechnic National University
Lviv Polytechnic National University

Benzoquinone and its reduced form hydroquinone belong to phenolic compounds and are found in living organisms in free form or in glycosides. They are active substances of some medicinal plants and have a pharmacological effect on the human body. Accordingly, their derivatives are important objects for chemical synthesis and development of new drugs. This article presents the findings of the structural design of substances with benzoquinone or hydroquinone fragment and sulfur-containing compound. By use of appropriate on-line programs a predictive screening of the biological activity and cytotoxicity of thiosulfonate derivatives of benzoquinone and hydroquinone has been conducted. It has been found that they have immense methodological potential to be synthesized by substances with a wide range of biological activities and a high value of probable activity, which substantiates the feasibility of conducting experimental studies on their biological activity, particularly anticancer.

1.  V. Dziuba, O. Kuchmenko ( 2017). Suchasni uiavlennia pro rol ubikhinonu v protsesakh metabolizmu klityny. Visnyk of the Lviv University. Series Biology. Issue 75. P. 3-13.
2. Linnane A., Kios M., Vitetta L. ( 2007). Coenzyme Q10 - its role as a prooxidant in the formation of superoxide anion/hydrogen peroxide and the regulation of the metabolome. Mitochondrion. Vol. 7s. P. 51-61,
3. Groneberg D., Kindermann B., Althammer M. et al.(2005). Coenzyme Q10 affects expression of genes involved in cell signaling, metabolism and transport in human CaCo-2 cells. Int. J. Biochem. Cell Biol. Vol. 37. N 6. P. 1208-1218.
4. N.I. Moskalenko, O.Z. Komarovska-Porokhniavets, O.P. Iskiv, N.Ie. Stadnytska. (2008). Biolohichni ta farmakolohichni aspekty khinoniv. Visn. Nats. un-tu "Lviv. Politekhnika". - 2008. - № 609. - S. 124-1305 Garlic. (2016) A potential source of pharmaceuticals and pesticides. A review/ Ravi Kant Upadhyay/International Journal of Green Pharmacy, 10(1), P. 124-130.
5. Lubenets V., Vasylyuk S., Monka N., Bolibrukh K., Komarovska-Porokhnyavets O.; Baranovych D., Musyanovych R., Zaczynska E.,Czarny A., Nawrot U. Novikov, V. (2017).Synthesis and antimicrobial properties of 4- acylaminobenzenethiosulfoacid S-esters. Saudi Pharmaceutical Journal 25, 266,
6. V. Lubenets, N. Stadnytska, D. Baranovych, S. Vasylyuk, O. Karpenko, V. Havryliak and V. Novikov (March 15th 2019). Thiosulfonates: The ProspectiveSubstances against Fungal Infections. In: Fungal Infection . Eds. Érico Silva de Loreto and Juliana Simoni Moraes Tondolo, Intech Open, London. DOI:10.5772/intechopen.84436.
7. Pylypets A. Z., Iskra R. Y., Havryliak V. V., Nakonechna A. V., Novikov V. P., Lubenets V. I. (2017) Effects of thiosulfonates on the lipid composition of rat tissues. Український біохімічний журнал. 89. 6, 58-64. doi:
8. Oriabinska L. B., Starovoitova S. О., Vasylyuk S.V., Novikov V. P., Lubenets V. I. (2017) Ethylthiosulfanilate effect on Candida tropicalis. Український біохімічний журнал. 89( 5). 70-76. doi:
9.T.I. Halenova, I.V. Nikolaeva, A.V. Nakonechna,K. B. Bolibrukh, N. Y. Monka, V. I. Lubenets, O. M.Savchuk, V. P. Novikov, L. I. Ostapchenko. (2015). The search of compounds with antiaggregation activity among S-esters of thiosulfonic acids. Ukr. Biochem. J. 87. 5.83-92. doi:
10. V. I. Lubenets, Stadnitskaya, V. P. Novikov. (2000) Synthesis of thiosulfonates belonging to quinoline derivatives. Russ. J. Org. Chem. 36, 851-853. DOI
11. Sato, R., Akutsu, Y., Goto, T., Saito, M. (1987). Benzopentathiepin as sulfurization reagent. Novel synthesis of thiosulfonates from sulfinates. Chem. Lett. 16. 2161-2162.
12. D. B. Baranovich, V. I. Lubenets, V. P. Novikov, (2001). Synthesis of thiosulfonates with functional groups in the aliphatic chain, Russ. J. Org. Chem. 37, 1046-1047.
13. D. B. Baranovich, V. I. Lubenets, V. P. Novikov (2001). Synthesis of S-[2-(4-Aminobenzenesulfonyl) ethyl] and S-[2-(3-Amino-4-methoxybenzenesulfonyl)ethyl] Thiosulfonates. Russ. J. Gen. Chem. 71, 1827- 1827. DOI
14. Q. Zhao, L. Lu, Q. (2017). Direct Monofluoromethylthiolation with S-(Fluoromethyl) Benzenesulfonothioate. Shen, Angew. Chem. 2017, 129, 11733-11736; Angew. Chem. Int. Ed. 56, 11575-11578. DOI:10.1002/anie.201705633
15. V. I. Lubenets, S. V. Vasylyuk, V. P. Novikov. (2005). Synthesis of S-(3-chloroquinoxalin-2-yl) esters of aliphatic and aromatic thiosulfonic acids. Chem. Heterocycl. Compd. 41, 1547-1548. 10.1007/s10593-006-0039-9
16. B. Chura, V. I. Lubenets, O. V. Goi, V. P. Novikov (2002). The Reaction of Sodium 4-Acetylaminobenzenethiosulfonate with 2,3-Dichloroquinoxaline. Chem. Heterocycl. Compd. 38, 1432-1433. DOI:10.1023/A:1022163417299
17. V. I. Lubenets, S. V. Vasylyuk, O. V. Goi, V. P. Novikov (2006). Reaction of 6,7-dichloroquinoline-5,8-quinone with thiosulfonic acid salts. Chem. Heterocycl. Compd. 42, 961-962. DOI
18. Lubenets V., Parashchyn Z., Vasylyuk S., Novikov V. (2017). The S-methyl-(2-methoxycarbonylaminobenzimidazole-5) thiosulfo-nate as potential anticancer agents. Global journal of Pharmacy & pharmaceutical Science. 3 (2). 001-003.
19. Shvets V, Karpenko O, Karpenko I,Novikov V, Lubenets V. (2017) Antimicrobial action of compositions based on thiosulfonates and biosurfactants on phytopathogens. Innovative Biosystems and Bioengineering. 1(1), 43-48.
20. І. А. Martyrosyan, O. V. Pakholyuk, B. D. Semak, O. Z. Komarovs'ka-Porokhnyavets', V. I. Lubenets', S. A. Pambuk. (2019). Novi tekhnolohiyi efektyvnoho zakhystu tekstylyu vid mikrobiolohichnykh poshkodzhen'. Nanosystemy, nanomaterialy, nanotekhnolohiyi.17( 4). 621-636 [in Ukrainian]
21. Roman Leontiev, Nils Hohaus, Claus Jacob, Martin C. H. Gruhlke & Alan J. Slusarenko A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin Scientific RePoRtS | (2018) 8:6763 | DOI:10.1038/s41598-018-25154-9.
 22 T. A. Gloriozova, D. A. Filimonov, A. A. Lagunin, V. V. Poroykov (1998) Testirovaniye komp'yuternoy sistemy dlya predskazaniya biologicheskoy aktivnosti PASS na vyborke novykh khimicheskikh soyedineniy. Khim.-farm. zhurnal. 32(12), 32-39. [in Russian]
23. A. Lagunin, A. Stepanchikova, D. Filimonov, V. Poroikov (2000). PASS: prediction of activity spectra for biologically active substances. Bioinformatics. 16 (8), 747-748.
24 Lagunin A. A., Dubovskaja V. I., Rudik A. V., Pogodin P. V., Druzhilovskiy D. S., Gloriozova T. A., Filimonov D. A., Sastry G. N., Poroikov V. V. CLC-Pred: a freely available web-service for in silico prediction of human cell line cytotoxicity for drug-like compounds. PLOS One, 2018, 13 (1), e0191838. DOI: 10.1371/journal.pone.0191838
25 Mampuys, P., McElroy, R., Clark, J., Orru, R., & Maesa, B. (2019) Thiosulfonates as Emerging Reactants: Synthesis and Applications. Adv. Synth. Catal., 362, 3 - 64.