Search and synthesis of antiviral agents among derivatives of nitrogen containing heterocycles
According to the scientific report at the meeting of the Presidium of the NAS of Ukraine, March 31, 2021
DOI:
https://doi.org/10.15407/visn2021.05.063Keywords:
oxazoles, thiazoles, oxoimidazolidines, pyrrolo[3,2-d]pyrimidines, imidazo[1,2-c]pyrimidines, pyrimido[1,6-a]pyrimidines, human papilloma virus, cytomegalovirus, poliovirus, polyomavirus, π-stackingAbstract
A number of new nitrogen-containing heterocyclic compounds have been synthesized and investigated against viruses causing opportunistic infections in humans (human cytomegalovirus, human papilloma virus, poliovirus and human polyomavirus). The most active compounds – "leader structures" were identified, they are characterized by a high level of inhibition of viral replication, and significant selectivity against cytomegalovirus, poliovirus and papilloma virus. The structure–activity relationship is studied.
References
Griffiths P., Baraniak I., Reeves M. The pathogenesis of human cytomegalovirus. J. Pathol. 2015. 235(2): 288–297. DOI: https://doi.org/10.1002/path.4437
Handler M.Z., Handler N.S., Majewski S., Schwartz R.A. Human papillomavirus vaccine trials and tribulations. J. Am. Acad. Dermatol. 2015. 73(5): 743-756. DOI: https://doi.org/10.1016/j.jaad.2015.05.040
Prado J.C.M., Monezi T.A., Amorim A.T., Lino V., Paladino A., Boccardo E. Human polyomaviruses and cancer: an overview. Clinics (San Paulo). 2018. 73(1): e558s. DOI: https://doi.org/10.6061/clinics/2018/e558s
Dalianis T., Eriksson B.-M., Felldin M., Friman V., Hammarin A.-L., Herthelius M., Ljungman P., Moln J., Wennberg L., Swartling L. Management of BK-virus infection – Swedish recommendations. Infect. Dis. (Lond.). 2019. 51(7): 479-484. DOI: https://doi.org/10.1080/23744235.2019.1595130
Fradet-Turcotte A., Archambault J. Recent advances in the search for antiviral agents against human papilloma-viruses. Antivir. Ther. 2007. 12(4): 431–451.
Ambalathingal G.R., Francis R.S., Smyth M.J., Smith C., Khanna R. BK Polyomavirus: Clinical Aspects, Immune Regu-lation, and Emerging Therapies. Clin. Microbiol. Rev. 2017, 30: 503–528. DOI: https://doi.org/10.1128/CMR.00074-16
Krishna B.A., Wills M.R., Sinclair J.H. Advances in the treatment of cytomegalovirus. Br. Med. Bull. 2019. 131(1): 5–17. DOI: https://doi.org/10.1093/bmb/ldz031
Riwar L.-J., Trapp N., Kuhn B., Diederich F. Substituent Effects in Parallel-Displaced p–p Stacking Interactions: Dis-tance Matters. Angew. Chem. Int. Ed. 2017. 56(37): 11252–11257. DOI: https://doi.org/10.1002/anie.201703744
Kachaeva M.V., Pilyo S.G., Kornienko A.M., Prokopenko V.M., Zhirnov V.V., Prichard M.N., Keith K.A., Yang G., Wang H.-K., Banerjee N.S., Chow L.T., Broker T.R., Brovarets V.S. In vitro Activity of Novel 1,3-Oxazole Derivatives against Human Papillomavirus. Ibnosina J. Med. Biomed. Sci. 2017. 9(4): 111–118. DOI: https://doi.org/10.4103/ijmbs.ijmbs_9_17
Drach B.S., Sviridov E.P., Kisilenko A.A., Kirsanov A.V. Zhurnal organicheskoi khimii. 1973. 9(9): 1818–1824 (in Russian).
Kornienko A.N., Pil’o S.G., Prokopenko V.M., Brovarets V.S. Synthesis of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlo-rides and N-substituted sulfonamides. Russ. J. Gen. Chem. 2012. 82(11): 1855–1858. DOI: https://doi.org/10.1134/S1070363212110229
Kornienko A.N., Pil’o S.G., Prokopenko V.M., Brovarets V.S. Amidophenacylating reagents in synthesis of new deriv-atives of 1,3-oxazole and 1,3-thiazole-4-sulfonyl chlorides and corresponding sulfonamides. Russ. J. Gen. Chem., 2014. 84(4): 686-692. DOI: https://doi.org/10.1134/S1070363214040148
Shablykin О.V., Kornii Y.E., Brovarets V.S., Shablykina O.V., Khilya V.P. Synthesis of new oxoimidazolidinе sulfona-mides with anticancer activity. Dopov. Nac. Akad. Nauk Ukr. 2019. (1): 79–85. DOI: https://doi.org/10.15407/dopovidi2019.01.079
Solomyannyi R.N., Slivchuk S.R., Vasilenko A.N., Rusanov E.B., Brovarets V.S. Synthesis of and preparation of relat-ed pyrrolo[3,2-d]pyrimidines. Russ. J. Gen. Chem. 2012. 82(2): 317–322. DOI: https://doi.org/10.1134/S1070363212020235
Solomyannyi R.N., Shablykina O.V., Moskvina V.S., Khilya V.P., Rusanov E.B., Brovarets V.S. 8-(Methyl(phenyl)sulfonyl)-2,6-dihydroimidazo[1,2-c]-pyrimidin-5(3Н)-ones and 9-(methyl(phenyl)sulfonyl)-2,3,4,7-dihydro-6H-pyrimido[1,6-a]pyrimidin-6-ones: synthesis and antiviral activity. Chem. Het. Comp., 2019, 55(4/5): 401–407. DOI: https://doi.org/10.1007/s10593-019-02472-y
Smee D.F., Hurst B.L., Evans W.J., Clyde N., Wright S., Peterson C., Jung K.-H., Day C.W. Evaluation of Cell Viability Dyes in Antiviral Assays with RNA Viruses that Exhibit Different Cytopathogenic Properties. J. Virol. Methods. 2017. 246: 51–57. DOI: https://doi.org/10.1016/j.jviromet.2017.03.012
Peirson S.N., Butler J.N. RNA extraction from mammalian tissues. Methods Mol. Biol. 2007. 362: 315–327. DOI: https://doi.org/10.1007/978-1-59745-257-1_22
Kachaeva M.V., Pilyo S.G., Hartline C.B., Harden E.A., Prichard M.N., Zhirnov V.V., Brovarets V.S. In vitro activity of novel derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile against human cytomegalovirus. Med. Chem. Res. 2019. 28(8): 1205–1211. DOI: https://doi.org/10.1007/s00044-019-02365-x
Kornii Yu., Chumachenko S., Shablykin O., Prichard M.N., James S.H., Hartline C., Zhirnov V., Brovarets V. New 2-Oxoimidazolidine Derivatives: Design, Synthesis and Evaluation of Anti-BK Virus Activities in Vitro. Chem. Biodiver-sity, 2019. 16: e1900391. DOI: https://doi.org/10.1002/cbdv.201900391
Solomyannyi R., Slivchuk S., Smee D., Choi J., Rusanov E., Zhirnov V., Brovarets V. In vitro Activity of the Novel Py-rimidines and Their Condensed Derivatives Against Poliovirus. Curr. Bioact. Compd. 2019. 15(5): 582–591. DOI: https://doi.org/10.2174/1573407214666180720120509
Solomyannyi R., Mitiukhin O., Prichard M., James S., Hartline C., Zhirnov V., Brovarets V. In vitro anti-BK polyoma-virus activity of imidazo[1,2-c]pyrimidine and pyrimido[1,6-a]pyrimidine derivatives. Curr. Chem. Lett. 2020. 9(2): 89–96. DOI: https://doi.org/10.5267/j.ccl.2019.9.001
