Predictive screening of the biological activity of S-alkyl esters of 8-quinolinsulfonic acid

2020;
: 125-134
1
National University Lviv Polytechnic
2
Lviv Polytechnic National University
3
Lviv Polytechnic National University
4
Lviv Polytechnic National University
5
Lviv Polytechnic National University

Quinoline and its derivatives are important compounds for the chemical synthesis and development of novel drugs. Practical application of a number of substances with quinoline heterocycle is already known in medical practice. We performed predictive screening for biological activity, cytotoxic and toxic effects on rats of synthesized 8-quinoline thiosulfonic acid S-alkyl esters using appropriate on-line programs.They have been found to be low-toxic substances with a broad spectrum of biological action and a high probability of activity, which indicates the expediency of continuing experimental studies of their properties. Particular attention should be paid to the methyl and ethyl esters of 8-quinolintiosulfonic acids.

1. O.D. Pietro, E. Vicente-García, M. C. Taylor, D. Berenguer, E.Viayna, A. Lanzoni, I. Sola, H. Sayago, C. Riera, R. Fisa, M. V.Clos, B. Pérez, J.M. Kelly, R. Lavilla, D.Muñoz-Torrero. (2015) Multicomponent reaction-based synthesis and biological evaluation of tricyclic heterofusedquinolines with multi-trypanosomatid activity. European Journal of Medicinal Chemistry. 105, 120-137.
https://doi.org/10.1016/j.ejmech.2015.10.007
2. Juan Carlos Coa, Wilson Castrillón, Wilson Cardona, Miguel Carda, Victoria Ospina, July Andrea Muñoz, Iván D. Vélez, Sara M. Robledo. (2015) Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids. European Journal of Medicinal Chemistry, 101, 746-753.
https://doi.org/10.1016/j.ejmech.2015.07.018
3. B. F. Abdel-Wahab, R. E. Khidre, and A. A. Farahat. (2011)Pyrazole-3(4)-carbaldehyde: synthesis, reactions and biological activity. Arkivoc, 1,. 196-245.
https://doi.org/10.3998/ark.5550190.0012.103
4. Mel'nikov N.N. (1987). Pestitsidi.Khimiya, tekhnologiya i primeneniye./ Mel'nikov N.N. Moskva: Khimiya, 712.
5. M.D. Mashkovs'kiy. (2001) Lekarstvennyye sredstva: V 2t T.2.-14-ye izd.,pererab., isp. i dop.-M.: OOO «Izdatel'stvo Novaya Volna»: Izdatel' S.B. Davidov, 2. 286.
6. Z. Cziaky, F. Korodi, L. Frank, and I. Czink (1996) Synthesis and antimycotic activity of new 2-chloro-3-(2-nitro)ethyl- and (2-nitro)vlnylquinolines. Heterocyclic Communications, 2(1), 63-70.
https://doi.org/10.1515/HC.1996.2.1.63
7. Delgado J N, Remers W A. Wilson and Gisvold's (1998). Text Book of Organic Medicinal and Pharmaceutical Chemistry, 10 th ed. Lippincott Williams & Wilkins. Text Book , 235-252.
8. A. M. Farghally, N. S. Habib, A. A. B. Hazzaa, and O. A. El-Sayed (1985) Synthesis of substituted quinoline-3-carbaldehyde (2,3- dihydrothiazol-2-ylidene) hydrazones of potential antimicrobial activity. Journal de Pharmacie de Belgique, 40(6), 366-372.
9. Fournet A, Barrios AA, Munoz V, Hocquemiller R, Cave A, Richomme P, Bruneton J. (1993). 2-Substituted quinoline alkaloids as potential antileishmanial drugs. Antimicrob Agents Chemother, 37, 859.
https://doi.org/10.1128/AAC.37.4.859
10. Bekhit A.A., El-Sayed O.A., Aboulmagd E., Park J.Y. (2004). Tetrazolo[1,5-a]quinoline as a potential promising new scaffold for the synthesis of novel anti-infl ammatory and antibacterial agents. Eur. J. Med. Chem, 39(3), 249-255.
https://doi.org/10.1016/j.ejmech.2003.12.005
11. R. Gupta, A. K. Gupta, S. Paul, and P. L. Kachroo (1998). Synthesis and biological activities of some 2-chloro-6/8-substituted-3-(3-alkyl/aryl-5,6-dihydro-s-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)quinolines. Indian Journal Of Chemistry B., 37, 1211-1213.
12. K.C. Nicolaou, J.L. Gross, M.A. Kerr (1996). Synthesis of novel heterocycles related to the Dynemicin A ring skeleton. J. Heterocycl. Chem.. 33(3), 735-746.
https://doi.org/10.1002/jhet.5570330336
13. Bringmann G, Reichert Y, Kane V. (2004). The total synthesis of streptonigrin and related antitumor antibiotic natural products. Tetrahedron. 60, 3539-3574.
https://doi.org/10.1016/j.tet.2004.02.060
14. H. L. Davis, D. D. Von Hoff, J. T. Henney, M. Rozencweig (1978). The role of antitumor antibiotics in current oncologic practice. Cancer Chemother. Pharmacol. 1(2), 83-90.
https://doi.org/10.1007/BF00254041
15. L. Kuz'menko, A. Avdeenko, S. Konovalova, S.Vasylyuk, O. Fedorova, N. Monka, A. Krychkovska, Vira Lubenets (2019). Synthesis and study of pesticidal activity of some N-arylthio-1,4-benzoquinone imines. Biointerface Research in Applied Chemistry. 9( 5), 4232 - 4238.
https://doi.org/10.33263/BRIAC95.232238
16. B. Mandal, B. Basu, RSC Adv. 2014, 4, 13854- 13881;, D. Witt, Synthesis 2008, 2491-2509
https://doi.org/10.1039/c3ra45997g
https://doi.org/10.1039/c3ra45997g
https://doi.org/10.1039/c3ra45997g
17. J. Yuan, C. Liu, A. Lei, Org. Chem. Front. 2015, 2, 677-680.
https://doi.org/10.1039/C5QO00027K
18. P. Mampuys, C. R. McElroy, J. H. Clark, R. V. A. Orru, B. U. W. Maesa, Thiosulfonates as Emerging Reactants: Synthesis and Applications. Adv. Synth. Catal. 2020, 362, 3-64 DOI: 10.1002/adsc.201900864
https://doi.org/10.1002/adsc.201900864
19. V. I. Lubenets, N. E. Stadnitskaya , V. P. Novikov (2000). Synthesis of thiosulfonates belonging to quinoline derivatives. Russian Journal of Organic Chemistry, 36(6), 851-853.
https://doi.org/10.1007/BF02757443
20. V. Lubenets, N. Stadnytska, D. Baranovych, S.Vasylyuk, O. Karpenko, V. HavryliakandV. Novikov (March 15th 2019). Thiosulfonates: The ProspectiveSubstances against Fungal Infections. In: Fungal Infection .Eds. Érico Silva de Loreto and JulianaSimoni Moraes Tondolo, IntechOpen, London. DOI:10.5772/intechopen.84436.
https://doi.org/10.5772/intechopen.84436
21. V. Lubenets, S.Vasylyuk, N. Monka, K. Bolibrukh, O.Komarovska-porokhnyavets, D. Baranovych, R. Musyanovych, E. Zaczynska, A. Czarny, U. Nawrot, V. Novikov (2017). Synthesis and antimicrobial properties of 4-acylaminobenzenethiosulfoacid S-esters. Saudi Pharmaceutical Journal, 25(2), 266-274. http://dx.doi.org/10.1016/j.jsps.2016.06.007
https://doi.org/10.1016/j.jsps.2016.06.007
22. Lubenets V.I., Stadnitskaya N.E., NovIkov V.P. (2000). Sintez tiosulfonatov - proizvodnih hinolina. Zhurn. org. Him, 36( 6), 883-885.
https://doi.org/10.1007/BF02757443
23. Stadnitska N.E., Lubenets V.I., NovIkov V.P., Komarovska O.Z., Vovk N.I., Krivoruchko O.M. (2000). Sintez ta bIologIchna aktivnIst S-alkIl(-8-hInolIn)tIosulfonatIv. Zhurn. fIzIologIchno aktivnih rechovin., 2(30) , 27-30.
24. T. A. Gloriozova, D. A. Filimonov, A. A. Lagunin, V. V. Poroykov (1998) Testirovanie kompyuternoy sistemyi dlya predskazaniya biologicheskoy aktivnosti PASS na vyiborke novyih himicheskih soedineniy. Him.-farm. zhurnal. 32(12), 32-39.
https://doi.org/10.1007/BF02641319
25. A. Lagunin, A. Stepanchikova, D. Filimonov, V. Poroikov (2000). PASS: prediction of activity spectra for biological lyactive substances. Bioinformatics. 16 (8), 747-748.
https://doi.org/10.1093/bioinformatics/16.8.747