Особливості взаємодії (бензо)імідазо[2,1-b][1,3]тіазинмезилатів з нуклеофільними реагентами

[1] Radini, A.M.; Abdel-Wahab, B.F.; Khidre, R.E. Synthetic Routes to Imidazothiazines. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 844-856. https://doi.org/10.1080/10426507.2015.1119148
[2] Goulart, T.A.C.; Kazmirski, J.A.G.; Back, D.F.; Zeni, G. Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides. J. Org. Chem. 2019, 84, 14113-14126. https://doi.org/10.1021/acs.joc.9b02276
[3] Ulomskiy, E.N.; Ivanova, A.V.; Gorbunov, E.B.; Esaulkova, I.L.; Slita, A.V.; Sinegubova, E.O.; Voinkov, E.K.; Drokin, R.A.; Butorin, I.I.; Gazizullina, E.R. et al. Synthesis and Biological Evalu-ation of 6-Nitro-1,2,4-triazoloazines Containing Polyphenol Frag-ments Possessing Antioxidant and Antiviral Activity. Bioorganic Med. Chem. Lett. 2020, 30, 127216. https://doi.org/10.1016/j.bmcl.2020.127216
[4] Abdel-Mohsen, H.T.; Abood, A.; Flanagan, K.J.; Meindl, A.; Senge, M.O.; Diwani, H.I.El. Synthesis, Crystal Structure, and ADME Prediction Studies of Novel Imidazopyrimidines as Antibacterial and Cytotoxic Agents. Arch. Pharm. 2020, 353, 1900271. https://doi.org/10.1002/ardp.201900271
[5] Demchenko, N.; Tkachenko, S.; Demchenko, S. Synthesis, Antibacterial and Anti-Corossive Activity of 2,3-Dihydroimidazo[1,2-a]pyridinium Bromides. Chem. Chem. Tech-nol. 2020, 14, 327-333. https://doi.org/10.23939/chcht14.03.327
[6] Muhammad, Z.A.; Farghaly, T.A.; Althagafi, I.; AlHussain, S.A.; Zaki, M.E.A.; Harras, M.F. Synthesis of Antimicrobial Azo-loazines and Molecular Docking for Inhibiting COVID-19. J. Heterocycl. Chem. 2021, 58, 1286-1301. https://doi.org/10.1002/jhet.4257
[7] Rodríguez, R.; Alejandro, O.; Vergara, M.; Sánchez, J.; Martínez, M.; Sandoval, Z.; Cruz, A.; Organillo, A. Synthesis, Crystal Structure, Antioxidant Activity and DFT Study of 2-Aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-One. J. Mol. Struct. 2020, 1199, 127036. https://doi.org/10.1016/j.molstruc.2019.127036
[8] Thompson, A.M.; Marshall, A.J.; Maes, L.; Yarlett, N.; Bacchi, C.J.; Gaukel, E.; Wring, S.A.; Launay, D.; Braillard, S.; Chatelain, E. et al. Assessment of a Pretomanid Analogue Library for African trypanosomiasis: Hit-to-Lead Studies on 6-Substituted 2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine 8-oxides. Bioorganic Med. Chem. Lett. 2018, 28, 207-213. https://doi: 10.1016/j.bmcl.2017.10.067
[9] Nikolova, I.; Slavchev, I.; Ravutsov, M.; Dangalov, M.; Nikolova, Y.; Zagranyarska, I.; Stoyanova, A.; Nikolova, N.; Mukova, L.; Grozdanov, P. et al. Anti-Enteroviral Activity of New MDL-860 Analogues: Synthesis, in vitro/in vivo Studies and QSAR Analysis. Bioorg. Chem. 2019, 85, 487–497. https://doi:10.1016/j.bioorg.2019.02.020
[10] Gong, J.-X.; He, Y.; Cui, Z.-L.; Guo, Y.-W. Synthesis, Spectral Characterization, and Antituberculosis Activity of Thiazino[3,2-а]benzimidazole Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 1036-1041. https://doi.org/10.1080/10426507.2015.1135149
[11] Thompson, A.M.; O’Connor, P.D.; Marshall, A.J.; Francisco, A.F.; Kelly, J.M.; Riley, J.; Read, K.D.; Perez, C.J.; Cornwall, S.; Thompson, R.C.A. et al. Re-Evaluating Pretomanid Analogues for Chagas disease: Hit-to-Lead Studies Reveal Both in vitro and in vivo Trypanocidal Efficacy. Eur. J. Med. Chem. 2020, 207, 112849. https://doi.org/10.1016/j.ejmech.2020.112849
[12] Meric, A.; Incesu, Z.; Hatipoglu, I. Synthesis of Some 3,4-Disubstituted-6,7-dihydroimidazo[2,1-b][1,3]thiazole and 3,4-Disubstituted-7,8-dihydro-6H-imidazo[2,1-b][1,3]thiazine Deriva-tives and Evaluation of their Cytotoxicities against F2408 and 5RP7 Cells. Med. Chem. Res. 2008, 17, 30-41. https://doi.org/10.1007/s00044-008-9090-7
[13] Schoeder, C.T.; Kaleta, M.; Mahardhika, A.B.; Olejarz-Maciej, A.; Łażewska, D.; Kieć-Kononowicz, K.; Müller, Ch.E. Structure-Activity Relationships of Imidazothiazinones and Analogs as Anta-gonists of the Cannabinoid-Activated Orphan G Protein-Coupled Receptor GPR18. Eur. J. Med. Chem. 2018, 155, 381-397. https://doi.org/10.1016/j.ejmech.2018.05.050
[14] Volkov, O.A.; Cosner, C.C.; Brockway, A.J.; Kramer, M.; Booker, M.; Zhong, Sh.; Ketcherside, A.; Wei, Sh.; Longgood, J.; McCoy, M. et al. Identification of Trypanosoma brucei AdoMetDC Inhibitors Using a High-Throughput Mass Spectrometry-Based Assay. ACS Infect. Dis. 2017, 3, 512-526. https://doi:10.1021/acsinfecdis.7b00022
[15] Litvinchuk, M.B.; Bentya, A.V.; Slyvka, N.Yu.; Vovk, M.V. Synthesis and Functionalization of 2-Alkylidene-5-(bromomethyl)-2,3-dihydro-1,3-thiazole Derivatives. Chem. Heterocycl. Compd. 2018, 54, 559-567. https://doi.org/10.1007/s10593-018-2304-0
[16] Saliyeva, L.M.; Vas’kevich, R.I.; Slyvka, N.Yu.; Vovk, M.V. The Synthesis and Structural Functionalization of 6-Substituted 2,3-dihydroimidazo[2,1-b][1,3]thiazol-5-ones. J. Org. Pharm. Chem. 2018, 16, 31-41. https://doi.org/10.24959/ophcj.18.940
[17] Shakh, Y.І.; Karkhut, А.І.; Bolibrukh, K.B.; Polovkovych, S.V. Rehioselektyvnist reaktsii nukleofilnoho zamishchennia mizh 5-zamishchenymy 1,4-naftokhinonamy ta aminotiotriazolamy. Khimiya, tekhnologiya rechovyn ta ih zastosuvannya 2015, 812, 210–217. (in Ukrainian)
[18] Sheldrick, G.M. A Short History of SHELX. Acta Crystallogr. A 2008, A64, 112-122. http://dx.doi.org/10.1107/S0108767307043930
[19] Kochergin, P.M.; Bagrii, A.K.; Galenko, A.K.; Kovpak, D.V.; Aleksandrova, E.V. Synthesis of 3-Halogeno Derivatives of Imida-zo[2,1-b]- and benzimidazo[2,1-b][1,3]thiazines. Chem. Heterocycl. Compd. 1997, 33, 882. https://doi.org/10.1007/BF02253051
[20] Saliyeva, L.; Slyvka, N.; Holota, S.; Grozav, A.; Yakovychuk, N.; Litvinchuk, M.; Vovk, M. Synthesis and Evaluation of Bioac-tivity of (2-Pyridinyloxy)substituted (benzo)imidazo[2,1-b][1,3]thiazines. Biointerface Res. Appl. Chem. 2022, 12, 5031-5044. https://doi.org/10.33263/BRIAC124.50315044
[21] Orlov, M.A.; Kapitanov, I.V.; Korotkikh, N I.; Shvaika, O.P. Synthesis and Recylization of 2,3,9,10-Tetrahydro-8H-[1,4]Dioxino[2,3-f]-[1,3]Thiazino[3,2-a]Benzimidazolium Salts. Chem. Heterocycl. Compd. 2014, 50, 111-116. https://doi.org/10.1007/s10593-014-1453-z
[22] Ouasif, L.; Ghoul, M.; Achour, R.; Saadi, M. 3,4-Dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3]thiazin-3-ol. IUCrData 2017, 2, x170429. https://doi.org/10.1107/S2414314617004291
[23] Gordon, A.J.; Ford, R.A. The Chemist’s Companion; Wiley-Interscience: New York, 1972.
[24] Novikov, R.V.; Danilkina, N.A.; Balova, I.A. Cyclocondensa-tion of n-(Prop-2-yn-1-yl)- and n-(Penta-2,4-diyn-1-yl)-o-phenylenediamines with Phenyl Isothiocyanate and Carbon Disul-fide. Chem. Heterocycl. Compd. 2011, 47, 758-766. https://doi:10.1007/s10593-011-0831-z
[25] Burgi, H.-B.; Dunitz, J.D. Structure correlation. Vol.2; VCH: Weinheim, 1994; pp 741-784.