![Synthesis and functionalization of pyrido[1,2-a]benzimidazole amino derivatives](/upload/12631c5e396938a702bdd516ae8c4208/issues/cover/028ab787bff7466421bec948e45337c9.png)
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Razrabotan prostoy sposob polucheniya aminoproizvodnyh pirido[1,2-a]benzimidazola. Predlozheny vozmozhnye puti ih dal'neyshey funkcionalizacii. Izucheny zakonomernosti reakcii nitrovaniya zameschennyh pirido[1,2-a]benzimidazolov.
Vosstanovitel'naya vnutrimolekulyarnaya geterociklizaciya, acilirovanie, reakciya SEAr, pirido[1,2-a]benzimidazol, hlorid N-(2-nitroaril)piridiniya
1. Darwish S.A.Z., Elbayaa R.Y., Ashour H.M.A., Khalil M.A., Badawey E.A.M. Potential Anticancer Agents: Design, Synthesis of New Pyrido[1,2-a]benzimidazoles and Related Derivatives Linked to Alkylating Fragments // Med. Chem. 2018. Vol. 8. P. 86-95. DOI:https://doi.org/10.4172/2161-0444.1000498.
2. Teng Q.-H., Peng X.-J., Mo Z.-Y., Xu Y.-L., Tang H.-T., Wang H.-S., Sun H.-B., Pan Y.-M. Transition-Metal-Free C-N and C-C Formation: Synthesis of Benzo[4,5]imidazo[1,2-a]pyridines and 2-Pyridones From Ynones // Green Chem. 2018. Vol. 20. P. 2007-2012. DOI:https://doi.org/10.1039/C8GC00069G.
3. Okombo J., Brunschwig C., Singh K., Dziwornu G.A., Barnard L., Njoroge M., Wittlin S., Chibale K. Antimalarial Pyrido[1,2-a]benzimidazole Derivatives with Mannich Base Side Chains: Synthesis, Pharmacological Evaluation and Reactive Metabolite Trapping Studies // ACS Infect. Dis. 2019. Vol. 5. P. 372–384. DOI:https://doi.org/10.1021/acsinfecdis.8b00279
4. Korkor C.M., Garnie L.F., Amod L., Egan T.J., Chibale K. Intrinsic Fluorescence Properties of Antimalarial Pyrido[1,2-a]benzimidazoles Facilitate Subcellular Accumulation and Mechanistic Studies in the Human Malaria Parasite Plasmodium falciparum // Org. Biomol. Chem. 2020. V. 18. P. 8668-8676. DOI:https://doi.org/10.1039/D0OB01730B.
5. 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.
6. Probst A., Chisanga K., Dziwornu G.A., Haeberli C., Keiser J., Chibale K. Expanding the activity profile of pyrido[1,2-a]benzimidazoles: Synthesis and evaluation of novel N1-1-phenylethanamine derivatives against Schistosoma mansoni // ACS Infect. Dis. 2021. Vol. 7. P. 1032–1043. DOI:https://doi.org/10.1021/acsinfecdis.0c00278.
7. Begunov R.S., Zayceva Yu.V., Sokolov A.A., Egorov D.O., Filimonov S.I. Sintez i antibakterial'naya aktivnost' 1,2,3,4-tetragidro- i pirido[1,2-a]benzimidazolov // Him.-farm. zhurn. 2022. T. 56, № 1. C. 25-31. DOI:https://doi.org/10.1007/s11094-022-02596-0.
8. Song G., Liu A., Jiang H., Ji R., Dong J., Ge Y. A FRET-based ratiometric fluorescent probe for detection of intrinsically generated SO2 derivatives in Mitochondria // Analytica Chimica Acta. 2019. Vol. 1053. P. 148-154. DOI:https://doi.org/10.1016/j.aca.2018.11.052.
9. Sagirli A. A new approach for the synthesis of fluorescent pyrido[1,2-a]benzimidazoles // Synthetic commun. 2020. Vol. 50. P. 3298-3307. DOI:https://doi.org/10.1080/00397911.2020.1800742.
10. Anderson J.C., Chang C.-H., Jathoul A.P., Syed A.J. Synthesis and bioluminescence of electronically modified and rotationally restricted colour-shifting infraluciferin analogues // Tetrahedron. 2019. Vol. 75. P. 347-356. DOI:https://doi.org/10.1016/j.tet.2018.11.061.
11. Weiwei Zhang, Hui-Jing Li, Meirong Wang, Li-Juan Wang, Ai-Han Zhang, Yan-Chao Wu. Highly effective inhibition of mild steel corrosion in HCl solution by using pyrido[1,2-a]benzimidazoles // New J. Chem. 2019. Vol. 43. P. 413-426. DOI:https://doi.org/10.1039/c8nj04028a.
12. Rachinskaya O.A., Popov K.V., Ryzvanovich G.A., Bol'sheva N.L., Begunov R.S., Yurkevich O.Yu., Zelenin A.V., Muravenko O.V. Povyshenie razreshayuschey sposobnosti hromosomnogo analiza s pomosch'yu pirido[1,2-a]benzimidazolov // Genetika. 2012. T. 48, № 10. S. 1228–1236. DOI:https://doi.org/10.1134/s1022795412100080.
13. Yang Kai, Luo Shi-He, Chen Si-Hong, Cao Xi-Ying, Zhou Yong-Jun, Lin Yan-Lan, Huo Yan-Ping, Wang Zhao-Yang. Simple inorganic base promoted C–N and C–C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid // Org. Biomol. Chem. 2021. Vol. 19. P. 8133 8139. DOI:https://doi.org/10.1039/D1OB01424B.
14. Leng J., Xin J., Zhou H., Li K., Hu W., Zhang Y. Theoretical insights into sensing performances of rhodamine-contained two-photon fluorescent probes for mercury ion // Int. J. Quantum Chem. 2021. Vol. 121. e26435. DOI:https://doi.org/10.1002/qua.26435.
15. Ge Y., Zheng X., Ji R., Shen S., Cao X. A new pyrido[1,2-a]benzimidazole-rhodamine FRET system as an efficient ratiometric fluorescent probe for Cu2+ in living cells // Anal. Chim. Acta. 2017. Vol. 965. P. 103-110. DOI:https://doi.org/10.1016/j.aca.2017.02.006.
16. Bodo Lipke. Zur Kenntnis von N-(Phenyl)-pyridiniumsalzen // Z. Chem. 1970. Vol. 10. P. 463. DOI:https://doi.org/10.1002/zfch.19700101207.
17. Begunov R.S., Sokolov A.A., Shebunina T.V. Vliyanie prirody vosstanavlivayuschego agenta na process vosstanovleniya hloridov N(2-nitrofenil)piridiniya // Zhurnal organicheskoy himii. 2013. T. 49. № 5. S. 789-791. DOI:https://doi.org/10.1134/S1070428013050291.
18. Begunov R.S., Sokolov A.A. Reakciya vosstanovitel'noy vnutrimolekulyarnoy geterociklizacii hloridov N-(2-nitroaril)piridiniya solyami metallov peremennoy valentnosti // Zhurnal organicheskoy himii. 2014. T. 50, № 8. S. 1234-1236. DOI:https://doi.org/10.1134/S1070428014080296.
19. Begunov R.S., Sokolov A.A., Sazhina A.A. Vliyanie temperatury i prirody protoniruyuschego agenta na vosstanovlenie hloridov N-(2-nitroaril)piridiniya // Zhurnal organicheskoy himii. 2015. T. 50, № 8. S. 1215-1217. DOI:https://doi.org/10.1134/S1070428015080266.
20. Begunov R.S., Sokolov A.A. Odnoreaktornoe vosstanovlenie i galogenirovanie N-(2,4-dinitrofenil)piperidina // Ot himii k tehnologii shag za shagom. 2022. T. 3, vyp. 2. S. 30-36. DOI:https://doi.org/10.52957/27821900_2022_02_30. URL: http://chemintech.ru/index.php/tor/2022tom3no2
