Synthesis of new imidazolidin-2-ones based on the reaction of 1-(2,2-dimethoxyethyl)urea with C-nucleophiles
- Авторлар: Smolobochkin A.1, Kuznetsova E.1, Gazizov A.1, Burilov A.1, Pudovik M.1
-
Мекемелер:
- Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
- Шығарылым: Том 93, № 6 (2023)
- Беттер: 835-839
- Бөлім: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/145059
- DOI: https://doi.org/10.31857/S0044460X23060021
- EDN: https://elibrary.ru/FJUKMS
- ID: 145059
Дәйексөз келтіру
Аннотация
The acid-catalyzed reaction of 1-(2,2-dimethoxyethyl)ureas with aromatic and heterocyclic nucleophiles leads to the formation of new imidazolidin-2-ones. The proposed method makes it quite easy to introduce the required pharmacophore group into position 4 of the imidazolidine cycle.
Негізгі сөздер
Авторлар туралы
A. Smolobochkin
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
Email: smolobochkin@iopc.ru
E. Kuznetsova
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
A. Gazizov
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
A. Burilov
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
M. Pudovik
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
Әдебиет тізімі
- Vitaku E., Smith D.T., Njardarson J.T. // J. Med. Chem. 2014. Vol. 57. P. 10257. doi: 10.1021/jm501100b
- Casnati A., Motti E., Mancuso R., Gabriele B., Della Ca' N. // Catalysts. 2019. Vol. 9. P. 28. doi: 10.3390/catal9010028
- Смолобочкин А.В., Газизов А.С., Бурилов А.Р., Пудовик М.А., Синяшин О.Г. // Усп. хим. 2021. Т. 90. С. 395
- Smolobochkin A.V., Gazizov A.S., Burilov A.R., Pudovik M.A., Sinyashin O.G. // Russ. Chem. Rev. 2021. Vol. 90. P. 395. doi: 10.1070/RCR4988
- Fu K.P., Neu H.C. // Antimicrob. Agents Chemother. 1978. Vol. 13. P. 930. doi: 10.1128/AAC.13.6.930
- Drusano G.L., Schimpff S.C., Hewitt W.L. // Clin. Infect. Diseases. 1984. Vol. 6. P. 13. doi: 10.1093/clinids/6.1.13
- Yamamoto D., Takai S., Jin D., Inagaki S., Tanaka K., Miyazaki M. // J. Mol. Cell. Cardiol. 2007. Vol. 43. P. 670. doi: 10.1016/j.yjmcc.2007.08.002
- Lewis R., Bagnall A.-M., Leitner M. // Cochrane Database of Systematic Reviews. 2005. N 3. P. 1. doi: 10.1002/14651858.CD001715.pub2
- Lee K.-C., Venkateswararao E., Sharma V.K., Jung S.-H. // Eur. J. Med. Chem. 2014. Vol. 80. P. 439. doi: 10.1016/j.ejmech.2014.04.048
- Lei H., Jiang N., Miao X., Xing L., Guo M., Liu Y., Xu H., Gong P., Zuo D., Zhai X. // Eur. J. Med. Chem. 2019. Vol. 171. P. 297. doi: 10.1016/j.ejmech.2019.03.038
- Gagné-Boulet M., Bouzriba C., Chavez Alvarez A.C., Fortin S. // J. Mol. Struct. 2022. Vol. 1259. P. 132691. doi: 10.1016/j.molstruc.2022.132691
- Robert J.-M.H., Sabourin C., Alvarez N., Robert-Piessard S., Le Baut G., Le Pape P. // Eur. J. Med. Chem. 2003. Vol. 38. P. 711. doi: 10.1016/S0223-5234(03)00119-3
- Alvarez N., Robledo S., Velez I.D., Robert J.M., Le Baut G., Le Pape P. // J. Enzyme Inhib. Med. Chem. 2002. Vol. 17. P. 443. doi: 10.1080/1475636021000005749
- Ammar A.Y., El-Sharief M.A.M.Sh., Ghorab M.M., Mohamed A.Y., Ragab A., Abbas Y.S. // Curr. Org. Synth. 2016. Vol. 13. P. 466. doi: 10.2174/1570179412666150817221755
- Gupta M., Ojha M., Yadav D., Pant S., Yadav R. // ACS Chem. Neurosci. 2020. Vol. 11. P. 2849. doi: 10.1021/acschemneuro.0c00403
- Kazmierski W.M., Furfine E., Gray-Nunez Y., Spaltenstein A., Wright L. // Bioorg. Med. Chem. Lett. 2004. Vol. 14. P. 5685. doi: 10.1016/j.bmcl.2004.08.038
- Goodacre C.J., Bromidge S.M., Clapham D., King F.D., Lovell P.J., Allen M., Campbell L.P., Holland V., Riley G.J., Starr K.R., Trail B.K., Wood M.D. // Bioorg. Med. Chem. Lett. 2005. Vol. 15. P. 4989. doi: 10.1016/j.bmcl.2005.08.004
- Rotstein D.M., Gabriel S.D., Manser N., Filonova L., Padilla F., Sankuratri S., Ji C., DeRosier A., Dioszegi M., Heilek G., Jekle A., Weller P., Berry P. // Bioorg. Med. Chem. Lett. 2010. Vol. 20. P. 3219. doi: 10.1016/j.bmcl.2010.04.077
- Li J., Sun Y., Chen Z., Su W. // Synth. Commun. 2010. Vol. 40. P. 3669. doi: 10.1080/00397910903531615
- Kochetkov K.A., Gorunova O.N., Bystrova N.A. // Molecules. 2023. Vol. 28. P. 602. doi: 10.3390/molecules28020602
- Hopkins B.A., Wolfe J.P. // Angew. Chem. Int. Ed. 2012. Vol. 51. P. 9886. doi: 10.1002/anie.201205233
- Casnati A., Perrone A., Mazzeo P.P., Bacchi A., Mancuso R., Gabriele B., Maggi R., Maestri G., Motti E., Stirling A., Della Ca' N. // J. Org. Chem. 2019. Vol. 84. P. 3477. doi: 10.1021/acs.joc.9b00064
- Sutherell C.L., Thompson S., Scott R.T.W., Hamilton A.D. // Chem. Commun. 2012. Vol. 48. P. 9834. doi: 10.1039/c2cc34791a
- Gazizov A.S., Smolobochkin A.V., Kuznetsova E.A., Abdullaeva D.S., Burilov A.R., Pudovik M.A., Voloshina A.D., Syakaev V.V., Lyubina A.P., Amerhanova S.K., Voronina J.K. // Molecules. 2021. Vol. 26. P. 4432. doi: 10.3390/molecules26154432
- Bosebabu B., Cheruku S.P., Chamallamudi M.R., Nampoothiri M., Shenoy R.R., Nandakumar K., Parihar V.K., Kumar N. // Mini-Rev. Med. Chem. 2020. Vol. 20. P. 988. doi: 10.2174/1389557520666200313120419
- Sucipto H., Wenzel S.C., Müller R. // ChemBioChem. 2013. Vol. 14. P. 1581. doi: 10.1002/cbic.201300289
- de Macedo M.B., Kimmel R., Urankar D., Gazvoda M., Peixoto A., Cools F., Torfs E., Verschaeve L., Lima E.S., Lyčka A., Milićević D., Klásek A., Cos P., Kafka S., Košmrlj J., Cappoen D. // Eur. J. Med. Chem. 2017. Vol. 138. P. 91. doi: 10.1016/j.ejmech.2017.06.061