Synthesis of new imidazolidin-2-ones based on the reaction of 1-(2,2-dimethoxyethyl)urea with C-nucleophiles
- Authors: Smolobochkin A.V1, Kuznetsova E.A1, Gazizov A.S1, Burilov A.R1, Pudovik M.A1
- 
							Affiliations: 
							- Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
 
- Issue: Vol 93, No 6 (2023)
- Pages: 835-839
- Section: Articles
- URL: https://rjeid.com/0044-460X/article/view/666946
- DOI: https://doi.org/10.31857/S0044460X23060021
- EDN: https://elibrary.ru/FJUKMS
- ID: 666946
Cite item
Abstract
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.
			                Keywords
About the authors
A. V 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. A Kuznetsova
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
A. S Gazizov
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
A. R Burilov
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
M. A Pudovik
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”
References
- 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
Supplementary files
 
				
			 
					 
						 
						 
						 
						 
									

 
  
  
  Email this article
			Email this article 
 Open Access
		                                Open Access Access granted
						Access granted Subscription or Fee Access
		                                							Subscription or Fee Access
		                                					