A New Method for Constructing Aryl-Substituted 3,3,4-Trihydroxy-2,3,4-Tetrahydrobenzimidazo[2,1-b][1,3]Thiazin-5-ium Salts
- Authors: Guseinov F.I.1,2, Kustov L.M.2, Afanasyeva K.A.1,2, Shuvalova E.V.2, Kobrakov K.I.1,2, Selyakin Y.L.3, Stepanov A.V.2, Samigullina A.I.2
-
Affiliations:
- Kosygin State University of Russia
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- MIREA-Russian Technology University (Lomonosov Institute of Fine Chemical Technology)
- Issue: Vol 61, No 10 (2025)
- Pages: 1474-1485
- Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
- URL: https://journals.rcsi.science/0514-7492/article/view/380883
- DOI: https://doi.org/10.7868/S3034630425100081
- ID: 380883
Cite item
Abstract
About the authors
F. I. Guseinov
Kosygin State University of Russia; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: guseinoveltos@mail.ru
ORCID iD: 0000-0002-6769-0232
Moscow, Russia
L. M. Kustov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
ORCID iD: 0000-0003-2312-3583
Moscow, Russia
K. A. Afanasyeva
Kosygin State University of Russia; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
ORCID iD: 0009-0007-3729-921X
Moscow, Russia
E. V. Shuvalova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
ORCID iD: 0000-0002-2657-7735
Moscow, Russia
K. I. Kobrakov
Kosygin State University of Russia; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
ORCID iD: 0000-0001-8940-0112
Moscow, Russia
Yu. L. Selyakin
MIREA-Russian Technology University (Lomonosov Institute of Fine Chemical Technology)
ORCID iD: 0000-0002-7027-378X
Moscow, Russia
A. V. Stepanov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
ORCID iD: 0009-0007-1797-2833
Moscow, Russia
A. I. Samigullina
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
ORCID iD: 0000-0002-6791-9973
Moscow, Russia
References
- Tariq S., Rahim, Ullah H.F., Sarfraz M., Hussain R., Khan S., Khan M.U., Rehman W., Hussain A., Bhat M.A., Farooqi M., Shah S., Iqbal N. Pharmaceuticals. 2024, 17, 410–431. https://doi.org/10.3390/ph17040410
- Naz H., Othman M., Rahim F., Hussain R., Khan S., Taha M., Hafez M., Abdel-Hafez L., Ullah H., Khan I., Khan Y., Shah S.A.A. J. Mol. Struct. 2024, 1312, 138592–138614. https://doi.org/10.1016/j.molstruc.2024.138592
- Hussain R., Ashraf M., Khan S., Rahim F., Rehman W., Taha M., Sardar A., Khan Y., Khan I., Shah S.A.A. J. Mol. Struct. 2024, 1295, 136582–136597. https://doi.org/10.1016/j.molstruc.2023.136582
- Barcin T., Yucel M.A., Ersan R.H., Alagoz M.A., Dogen A., Burmaoglu S., Algul O. J. Mol. Struct. 2024, 1295, 136668–136680. https://doi.org/10.1016/j.molstruc.2023.136668
- Dampalla C.S., Miller M.J., Kim Y., Zabiegala A., Nguyen H.N., Madden T.K., Thurman H., Machen A.J., Cooper A., Liu L., Battaille K.P., Lovell S., Chang K.-O., Groutas W.C. Eur. J. Med. Chem. 2023, 254, 115376–115394. https://doi.org/10.1016/j.ejmech.2023.115376
- Zaręba P., Drabczyk A. K., Wnorowska S., Wnorowski A., Jaśkowska J. Bioorg. Chem. 2023, 139, 106730–106744. https://doi.org/10.1016/j.bioorg.2023.106730
- Du K., Wang X., Bai Y., Zhang X., Xue J., Li S., Xie Y., Sang Z., Tang Y., Wang X. Eur. J. Med. Chem. 2024, 271, 116402–116421. https://doi.org/10.1016/j.ejmech.2024.116402
- Noor A., Qazi N.G., Nadeem H., Khan A.-U., Paracha R.Z., Ali F., Saeed A. Chem. Cent. J. 2017, 11, 1–13. https://doi.org/10.1186/s13065-017-0314-0
- Gangula S., Elati C.R., Neredla A., Baddam S.R., Neelam U.K., Bandichhor R., Dongamanti A. Org. Proc. Res. Dev. 2010, 14, 229–233. https://doi.org/10.1021/op900258b
- Deswal L., Verma V., Kirar J.S., Kumar D., Deswal Y., Kumar A., Bhatia M. Res. Chem. Intermed. 2023, 49, 1059–1083. https://doi.org/10.1007/s11164-022-04921-4
- Sharaf M., Moustafa A.H., Obaid R.J., Alzahrani A.Y., Aboelez M.O., Elkady H., Alenazi N.A., Mohamed M.A.A., Al-Fahemi J.H., Moussa Z., Omran O.A., Ahmed S.A. J. Mol. Struct. 2024, 1295, 136708–136724. https://doi.org/10.1016/j.molstruc.2023.136708
- Meduri B., Pavan S.R., Prabhu A., Shankaranarayana A.H., Sethu A.K., Singh M., Pujar K.G., Siddappa R.S., Bidye D., Pujar G.V. J. Mol. Struct. 2024, 1295, 136672–136685. https://doi.org/10.1016/j.molstruc.2023.136672
- Akbarzadeh M., Bakavoli M., Eshghi H., Shiri A. J. Chem. Res. 2017, 41, 730–733. https://doi.org/10.3184/174751917X15132496997778
- Eldeha W.M., El Hassab M.A., Abo-Ashour M.F., Al-Warhi T., Elaasser M.M., Safwat N.A., Suliman H., Ahmed M.F., Al-Rashood S.T., Abdel-Aziz H.A., El-Haggar R. Bioorg. Chem. 2021, 110, 104748–104761. https://doi.org/10.1016/j.bioorg.2021.104748
- Ersan R.H., Alagoz M.A., Erran-Bolelli T., Duran N., Burmaoglu S., Algul O. Mol. Div. 2021, 25, 2247–2259. https://doi.org/10.1007/s11030-020-10115-0
- Chen W.L., Chen X., Guo X. K., Jiang Z. Y., Li D.D., Wang Y.Z., Xu J.J., You Q.D. Eur. J. Med. Chem. 2020, 188, 112027–112033. https://doi.org/10.1016/j.ejmech.2019.112027
- Jiang L., Peng P., Yu L., Jiang D., Wang Y., Li H., Yuan M., Yuan M. Tetrahedron. 2021, 98, 132430–132439. https://doi.org/10.1016/j.tet.2021.132430
- Abele E., Abele R., Arsenyan P., Belyakov S., Veiveris M., Lukevics E. Chem. Heterocycl. Compd. 2007, 43, 220–224. https://doi.org/10.1007/s10593-007-0034-9
- Goni L.K., Jafar Mazumder M.A., Quraishi M.A., Mizanur Rahman M. Chem. Asian J. 2021, 16, 1324–1364. https://doi.org/10.1002/asia.202100201
- Batooie N., Khodaei M.M., Bahrami K., Miraghaee S.S., Hosseinzadeh N., Sajadimajad S. J. Molec. Struct. 2023, 1271, 134037–134044. https://doi.org/10.1016/j.molstruc.2022.134037
- He Z.Q., Chen S.J., Chen G.S., Lin J.H., Wu J.M., Liu Y. L. J. Org. Chem. 2023, 88, 13262–13271. https://doi.org/10.1021/acs.joc.3c01570
- Jing-Xu G., Ya H., Zhen-Lin C., Yue-Wei G. Phosphorus, Sulfur, Silicon Relat. Elem. 2016, 191, 1036–1041. https://doi.org/10.1080/10426507.2015.1135149
- Galal S.A., Naem S.I.E., Nezhawy A.O.E., Ali M.A., Diwani H.I.E. Arch. Pharm. Chem. Life Sci. 2011, 11, 255–263. https://doi.org/10.1002/ardp.201000252
- Guseinov F.I., Movsumzade E.M., Kustov L.M., Malinnikov V.M., Pistov M.F., Lavrova O.M. Mendeleev Commun. 2020, 5, 674–675. https://doi.org/10.1016/j.mencom.2020.09.041
- Гусейнов Ф.И., Бурангулова Р.Н., Мухамедзянова Е.Ф., Струнин Б.П., Синяшин О.Г., Литвинов И.А., Губайдуллин А.Т. Химия гетероциклических соединений. 2006, 7, 943–947.
- Guseinov F.I., Pistov M.F., Movsumzade E.M., Kustov L.M., Tafeenko V. A., Chernyshev V.V., Pombeiro A.J. Crystals. 2017, 11, 327–335. https://doi.org/10.3390/cryst7100327
- Guseinov F.I., Ovsyannikov V.O., Shuvalova E.V., Samigullina A.I., Mahmudov K.T. New J. Chem. 2024, 48, 12869–12872. https://doi.org/10.1039/D4NJ01789G
- Гусейнов Ф.И., Тагиев С.Ш. Журнал органической химии. 1995, 31, 86–89.
- Гусейнов Ф.И., Юдина Н.А. Химия гетероциклических соединений. 1998, 34, 115–120.
- Dubey T., Kate P., Karale R., Sawale V. Int. J. Pharm. Sci. 2024, 2, 10–20. https://doi.org/10.5281/zenodo.11409656
- Adhikari A., Bhakta S., Ghosh T. Tetrahedron. 2022, 126, 133085–133109. https://doi.org/10.1016/j.tet.2022.133085
- Henary M., Kananda C., Rotolo L., Savino B., Owens E.A., Cravotto G. RSC Adv. 2020, 10, 14170–14197. https://doi.org/10.1039/D0RA01378A
- Amrutkar S.V., Chikhale H.U., Dandagavhal K.R., Mali D. R. Int. J. ChemTech Res. 2017, 10, 305–310.
- Jiang L., Peng P., Yu L., Jiang D., Wang Y., Li H., Yuan M., Yuan M. Tetrahedron. 2021, 98, 132430–132439. https://doi.org/10.1016/j.tet.2021.132430
- Kumar R., Nair R.R., Prakash R., Bae T., Dohi T., Prakash O. Letters in Organic Chemistry. 2024, 21, 209–212. https://doi.org/10.2174/1570178620666230803123511
- Misiunaitė I., Bukšnaitienė R., Pošiūnas J., Brukštus A., Žutautė I. J. Heterocycl. Chem. 2022, 59, 1712–1722. https://doi.org/10.1002/jhet.4499
- Saliyeva L.M., Slyvka N.Y., Korotkykh M.I., Vovk M.V. Chem. Heterocycl. Compd. 2023, 59, 368–385. https://doi.org/10.1007/s10593-023-03206-x
- Nguyen P.H., Hue B.T., Pham M.Q., Hoa T.P., Tran Q. De, Jung H., Hieu L.T., Quoc N.C., Quan H.V., Quy N.P., Yoo H.J., Yang S.G. New J. Chem. 2023, 47, 7622–7633.
- Allen F.H., Кennard O., Watson D.G., Brammer L., Orpen A.G., Тaylor R.J. Chem. Soc., Perkin Тrans. 1987, 2, S1–S19. https://doi.org/10.1039/P298700000S1
- CrysAlisPro. Version 1.171.41.106a. Rigaku Oxford Diffraction, 2021.
- Sheldrick G.M. Acta Cryst. 2015, A71, 3–8. https://doi.org/10.1107/s2053273314026370
- Sheldrick G.M. Acta Cryst. 2015, C71, 3–8. https://doi.org/10.1107/S2053229614024218
- Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K. J. Appl. Cryst. 2009, 42, 339–341. https://doi.org/10.1107/S0021889808042726
- Macrae C.F., Sovago I., Cottrell S.J., Galek P.T., McCabe P., Pidcock E., Platings M., Shields G.P., Stevens J.S., Towler M., Wood P.A. J. Appl. Cryst. 2020, 53, 226–235. https://doi.org/10.1107/S1600576719014092
Supplementary files


