![Regioselektivnost` reakcii galogenirovaniya 9-xlorpirido[1,2-a]benzimidazola](/upload/12631c5e396938a702bdd516ae8c4208/issues/cover/d2fc3864dd0e37304717f34bbb6953a6.jpeg)
employee
Yaroslavl, Yaroslavl, Russian Federation
student
Yaroslavl, Yaroslavl, Russian Federation
Metodami eksperimental'noy i kvantovoy himii izuchena regioselektivnost' reakcii SEAr 9-hlorpirido[1,2-a]benzimidazola. Process galogenirovaniya provodili v sernoy kislote, ispol'zuya N-bromsukcin- ili N-hlorsukcinimid. Proishodilo obrazovanie dvuh izomernyh produktov 8-Hal-9-hlorpirido[1,2-a]benzimidazola i 6-Hal-9-hlorpirido[1,2-a]benzimidazola. Preimuschestvenno vvedenie elektrofil'noy chasticy proishodilo v 8-e polozhenie geterocikla. S pomosch'yu metodov kvantovoy himii ustanovleno, chto reakciya elektrofil'nogo galogenirovaniya imela orbital'nyy kontrol'. Orientaciya vvedeniya elektrofil'noy chasticy opredelyalas' raspredeleniem granichnoy elektronnoy plotnosti v substrate, chto horosho soglasovyvalos' s eksperimental'nymi dannymi.
9-hlorpirido[1,2-a]benzimidazol, N-galogensukcinimid, reakciya SEAr, regioselektivnost', kvantovo-himicheskoe modelirovanie, metod DFT B3LYP/6-31G**, programmnyy kompleks PC GAMESS/Firefly i ORCA 5.0.4
1. Mayoka G., Keiser J., Häberli C., Chibale K. Structure–Activity Relationship and in Vitro Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) Studies of N-aryl 3-Trifluoromethyl Pyrido[1,2-a]benzimidazoles That Are Efficacious in a Mouse Model of Schistosomiasis // ACS Infect. Dis. 2019. Vol. 5. P. 418–429. DOI:https://doi.org/10.1021/acsinfecdis.8b00313.
2. Liu A., Ji R., Shen S., Cao X., Ge,Y. A ratiometric fluorescent probe for sensing sulfite based on a pyrido [1, 2 a] benzimidazole fluorophore // New Journal of Chemistry. 2017. Vol. 41, no. 18. P. 10096-10100. DOI:https://doi.org/10.1039/C7NJ02086D.
3. Gadde S., Kleynhans A., Holien J.K., Bhadbhade M., Nguyen P.L. D., Mittra R., Yu T.T., Carter D.R., Parker M.W., Marshall G.M., Cheung B.B., Kumar N. Pyrimido[1,2-a]benzimidazoles as inhibitors of oncoproteins ubiquitin specific protease 5 and MYCN in the childhood cancer neuroblastoma // Bioorg Chem. 2023. Vol. 136. No.106462. DOI:https://doi.org/10.1016/j.bioorg.2023.106462.
4. Kotovskaya S.K., Baskakova Z.M., Charushin V.N., Chupahin O.N., Belanov E.F., Bormotov N.I., Balahnin S.M., Serova O.A. Sintez i protivovirusnaya aktivnost' ftorsoderzhaschih proizvodnyh pirido[1,2-a]benzimidazolov. Him.-farm. zhurnal. 2005. T. 39, № 11. S. 12–16. DOI:https://doi.org/10.30906/0023-1134-2005-39-11-12-16
5. Arutyunyan A.A., Avakimyan Dzh.A., Stepanyan G.M. Antibakterial'nye svoystva nekotoryh policiklicheskih geterociklov na osnove pirimidina i benzimidazola // Biolog. zhurnal Armenii. 2016. Vol. 68, iss. 2. S. 88–91. URL: https://arar.sci.am/dlibra/publication/260297
6. Koo H.L., Dupont H.L. Rifaximin: A Unique Gastrointestinal-Selective Antibiotic for Enteric Diseases // Curr. Opin. Gastroenterol. 2010. Vol. 26. P. 17–25. DOI:https://doi.org/10.1097/MOG.0b013e328333dc8d.
7. Begunov R.S., Egorov D.O., Chetvertakova A.V., Savina L.I., Zubishina A.A. Antibakterial'naya aktivnost' galogen- i nitroproizvodnyh benzimidazola v otnoshenii Bacillus subtilis // Antibiotiki i himioterapiya. 2023. T. 68, № 3-4. S. 19-24. DOI:https://doi.org/10.37489/0235-2990-2023-68-3-4-19-24.
8. Andrzejewska M., Yépez-Mulia L., Cedillo-Rivera R., Tapia A., Vilpo L., Vilpo J., Kazimierczuk Z. Synthesis, antiprotozoal and anticancer activity of substituted 2- trifluoromethyl- and 2 pentafluoroethylbenzimidazoles // European Journal of Medicinal Chemistry. 2002. Vol. 37. P. 973–978. DOI:https://doi.org/10.1016/S0223-5234(02)01421-6.
9. Tkachenko P.V., Tkachenko E.V., Zhuravel' I.A., Kazmirchuk V.V., Derbisbekova U.B. Sintez i protivomikrobnaya aktivnost' 4-arilsul'fanilproizvodnyh 5-aminopirazolov // Vestnik KazNMU. 2017. №2. S. 307–311. URL: https://cyberleninka.ru/article/n/sintez-i-protivimikrobnaya-aktivnost-4-arilsulfonilproizvodnyh-5-aminopirazolov
10. Begunov R.S., Sokolov A.A., Belova V.O., Fakhrutdinov A.N., Shashkov A.S., Fedyanin I.V. Reaction of substituted pyrido[1,2-a]benzimidazoles with electrophilic agents // Tetrahedron Letters. 2015. Vol. 56, iss. 42. P. 5701–5704. DOI:https://doi.org/10.1016/j.tetlet.2015.08.014.
11. Begunov R.S., Ryzvanovich G.A., Firgang S.I. Prostoy sposob sinteza zameschennyh benzo[4,5]imidazo[1,2-a]piridinov // Zhurnal organicheskoy himii. 2004. T. 40, № 11. S. 1740-1742. DOI:https://doi.org/10.1007/s11178-005-0082-5.
12. Bogdanova D.M., Savina L.I., Begunov R.S. Sintez i funkcionalizaciya aminoproizvodnyh pirido[1,2-a]benzimidazola // Ot himii k tehnologii shag za shagom. 2022. T. 3, № 4. S. 30-38. URL: https://chemintech.ru/ru/nauka/issue/5030/view
13. Becke A. D. Density-functional thermochemistry. III. The role of exact exchange // J. Chem. Phys. 1993. Vol. 98, no. 7. P. 5648-5652. DOI:https://doi.org/10.1063/1.464913.
14. Miehlich B. A., Savin H. S., Stoll H, Preuss H. Results Obtained with the Correlation Energy Density Functionals of Becke and Lee, Yang and Parr // Chemical Physics Letters. Vol. 157, no. 3. 1989. P. 200-206. DOI:https://doi.org/10.1016/0009-2614(89)87234-3.
15. Mueller M. Fundamentals of Quantum Chemistry. Molecular Spectroscopy and Modern Electronic Structure Computation // International Journal of Molecular Sciences. Vol. 2, no. 6. P. 291-292. DOI:https://doi.org/10.3390/i2060291.
16. Granovsky A. A. Firefly version 8.8. URL: http://classic.chem.msu.su/gran/firefly/index.html
17. Neese F. The ORCA program system // Wiley Interdisciplinary Reviews: Computational Molecular Science. 2012. Vol. 2, no. 1. P. 73–78. DOI:https://doi.org/10.1002/wcms.81.
18. Fukui K., Yonezawa T., Nagata C. MO-Theoretical Approach to the Mechanism of Charge Transfer in the Process of Aromatic Substitutions // Bulletin of the Chemical Society of Japan. 1957. Vol. 27. P. 1247-1256. DOIhttps://doi.org/10.1063/1.1743986.
19. Breza M., Milata V. Quantum-chemical studies of the nitration of benzazoles // ARKIVOC. 2005. Vol. 9. P. 80–89. DOI:https://doi.org/10.3998/ark.5550190.0006.909.
20. Bode B.M., Gordon M.S. MacMolPlt: a graphical user interface for GAMESS // J. Mol. Graphics and Modeling. 1998. Vol. 16, no. 3. P. 133-138. DOI:https://doi.org/10.1016/s1093-3263(99)00002-9).
21. Zhurko G.A. Chemcraft. Version 1.6. URL: http://www.chemcraftprog.com
