Diels–Alder Adducts of N-Substituted 2-Pyridones with Maleinimides. Synthesis and Antiviral Activity
- Авторлар: Sorokina V.A.1, Kovalskaya A.V.1, Lobov A.N.1, Ilyina P.A.2, Zarubaev V.V.2, Tsypysheva I.P.1
- 
							Мекемелер: 
							- Ufa Federal Research Center of the Russian Academy of Sciences
- Saint Petersburg Pasteur Institute
 
- Шығарылым: Том 94, № 6 (2024)
- Беттер: 691-698
- Бөлім: Articles
- URL: https://rjpbr.com/0044-460X/article/view/667381
- DOI: https://doi.org/10.31857/S0044460X24060024
- EDN: https://elibrary.ru/FAESAH
- ID: 667381
Дәйексөз келтіру
Аннотация
Adducts of N-substituted 2-pyridones [pyridine-2(1H)-ones] and N-substituted maleic acid imides were synthesized under thermal conditions of the Diels–Alder reaction with yields from 68 to 97%. Cytotoxicity and antiviral activity of the obtained compounds were studied using a model of adenovirus infection [human adenovirus type 5 (AdV5)] in MA-104 cell culture. It was shown that the synthesized adducts have low toxicity and medium antiviral activity. Only 9-hexyl-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-(epiminomethano)isoindole-1,3,8-trione has the most pronounced viral inhibitory properties with a selectivity index of 7.
Негізгі сөздер
Толық мәтін
 
												
	                        Авторлар туралы
V. Sorokina
Ufa Federal Research Center of the Russian Academy of Sciences
														Email: tsypysheva.ip@gmail.com
				                	ORCID iD: 0000-0001-5311-9580
				                																			                												                	Ресей, 							Ufa						
A. Kovalskaya
Ufa Federal Research Center of the Russian Academy of Sciences
														Email: tsypysheva.ip@gmail.com
				                	ORCID iD: 0000-0001-7772-2894
				                																			                												                	Ресей, 							Ufa						
A. Lobov
Ufa Federal Research Center of the Russian Academy of Sciences
														Email: tsypysheva.ip@gmail.com
				                	ORCID iD: 0000-0002-9223-508X
				                																			                												                	Ресей, 							Ufa						
P. Ilyina
Saint Petersburg Pasteur Institute
														Email: tsypysheva.ip@gmail.com
				                					                																			                												                	Ресей, 							Saint Petersburg						
V. Zarubaev
Saint Petersburg Pasteur Institute
														Email: tsypysheva.ip@gmail.com
				                	ORCID iD: 0000-0002-6837-5242
				                																			                												                	Ресей, 							Saint Petersburg						
I. Tsypysheva
Ufa Federal Research Center of the Russian Academy of Sciences
							Хат алмасуға жауапты Автор.
							Email: tsypysheva.ip@gmail.com
				                	ORCID iD: 0000-0002-5025-8742
				                																			                												                	Ресей, 							Ufa						
Әдебиет тізімі
- Российский терапевтический справочник / Под ред. А.Г. Чучалина. М.: ГЭОТАР-Медиа, 2005. 860 с.
- Arnold A., MacMahon E. // Medicine. 2021. Vol. 49. N 12. P. 790. doi: 10.1016/j.mpmed.2021.09.013
- Rowe W.P., Huebner R.J., Gilmore L.K., Parrott R.H., Ward T.G. // Proc. Soc. Exp. Biol. Med. 1953. Vol. 84. N 3. P. 570. doi: 10.3181/00379727-84-20714
- Binder A.M., Bigg H.M., Hayne A.K., Chommanard C., Lu X., Erdma D.D., Watson J., Gerber S.I. // Morb. Mortal. Wkly. Rep. 2017. Vol. 66. P. 1039. doi: 10.15585/mmwr.mm6639a2
- Munoz F.M., Piedra P.A., Demmler G.J. // Clin. Infect. Dis. 1998. Vol. 27. N 5. P. 1194. doi: 10.1086/514978
- Abzug M.J., Levin M.J. // Pediatrics. 1991. Vol. 87. N 6. P. 890.
- Rosario R.F., Kimbrough R.C., Van Buren D.H., Laski M.E. // Transpl. Infect. Dis. 2006. Vol. 8. N 1. P. 54. doi: 10.1111/j.1399-3062.2006.00137.x
- Abarca V.K., Le Corre P.N., Perret P.C., Wietstruck P.A., Oddó B.D., Barriga C.F. // Rev. Chilena Infectol. 2008. Vol. 25. N 2. P. 127.
- Hierholzer J.C. // Clin. Microbiol. Rev. 1992. Vol. 5. N 3. P. 262. doi: 10.1128/CMR.5.3.262
- Cox M.M. // Yale J. Biol. Med. 2005. Vol. 78. N 5. P. 321.
- Cesaro S., Porta F. // J. Clin. Med. 2022. Vol. 11. N 16. P. 4827. doi: 10.3390/jcm11164827
- Mazzotta S., Berastegui-Cabrera J., Vega-Holm M., García-Lozano M.D.R., Carretero-Ledesma M., Aiello F., Vega-Pérez J.M., Pachón J., Iglesias-Guerra F., Sánchez-Céspedes J. // Bioorg. Chem. 2021. Vol. 114. P. 105095. doi: 10.1016/j.bioorg.2021.105095
- Ehlert K., Schulte J.H., Kühl J.S., Lang P., Eggert A., Voigt S. // J. Pediatric Infect. Dis. Soc. 2021. Vol. 10. N 11. P. 987. doi: 10.1093/jpids/piab072
- Dahal S., Cheng R., Cheung P.K., Been T., Malty R., Geng M., Manianis S., Shkreta L., Jahanshahi S., Toutant J., Chan R., Park S., Brockman M.A., Babu M., Mubareka S., Mossman K., Banerjee A., Gray-Owen S., Brown M., Houry W.A., Chabot B., Grierson D., Cochrane A. // Viruses. 2022. Vol. 14. P. 60. doi: 10.3390/v14010060
- Nikitenko N.A., Gureeva E.S., Ozerov A.A., Tukhvatulin A.I., Izhaeva F.M., Prassolov V.S., Deryabin P.G., Novikov M.S., Logunov D.Y. // Acta Naturae. 2018. Vol. 10. N 2. P. 58.
- Kang D., Zhang H., Zhou Z., Huang B., Naesens L., Zhan P., Liu X. // Bioorg. Med. Chem. Lett. 2016. Vol. 26. N 21. P. 5182. doi: 10.1016/j.bmcl.2016.09.071
- Sánchez-Céspedes J., Martínez-Aguado P., Vega-Holm M., Serna-Gallego A., Candela J.I., Marrugal-Lorenzo J.A., Pachón J., Iglesias-Guerra F., Vega-Pérez J.M. // J. Med. Chem. 2016. Vol. 59. N 11. P. 5432. doi: 10.1021/acs.jmedchem.6b00300
- Mazzotta S., Marrugal-Lorenzo J.A., Vega-Holm M., Serna-Gallego A., Álvarez-Vidal J., Berastegui-Cabrera J., Pérez Del Palacio J., Díaz C., Aiello F., Pachón J., Iglesias-Guerra F., Vega-Pérez J.M., Sánchez-Céspedes J. // Eur. J. Med. Chem. 2020. Vol. 185. P. 111840. doi 10.1016/ j.ejmech.2019.111840
- Fedorova V.A., Kadyrova R.A., Slita A.V., Muryleva А.A., Petrova P.R., Kovalskaya A.V., Lobov A.N., Tsypyshev D.O., Borisevich S.S., Tsypysheva I.P., Zileeva Z.R., Vakhitova J.V., Zarubaev V.V. // Nat. Prod. Res. 2021. Vol. 35. P. 4256. doi: 10.1080/14786419.2019.1696791
- Tsypysheva I.P., Lai Hs.-Ch., Kiu Y.-T., Koval’skaya A.V., Tsypyshev D.O., Huang S.-H., Lin Ch.-W. // Bioorg. Med. Chem. Lett. 2021. Vol. 54. P. 128437. doi 10.1016/ j.bmcl.2021.128437
- Lin C.S., Lu C.H., Lin T.H., Kiu Y.T., Kan J.Y., Chang Y.J., Hung .PY., Koval’skaya A.V., Tsypyshev D.O., Tsypysheva I.P., Lin C.W. // Bioorg. Med. Chem. Lett. 2024. Vol. 99. P. 129623. doi: 10.1016/j.bmcl.2024.129623
- Tsypysheva I., Koval’skaya A., Petrova P., Lobov A., Borisevich S., Tsypyshev D., Fedorova V., Gorbunova E., Galochkina A., Zarubaev V. // Tetrahedron. 2019. Vol. 75. P. 2933. doi: 10.1016/j.tet.2019.04.021
- Фарафонтова-Антипина Е.И., Ковальская А.В., Петрова П.Р., Сайфутдиярова Р.Р., Цыпышев Д.О., Федорова В.А., Лобов А.Н., Борисевич С.С. // Вестн. Башкирск. унив. 2018. № 1. С. 27.
- Afarinkia K., Vinader V., Nelson T.D., Posner G.H. // Tetrahedron. 1992. Vol. 48. N 42. P. 9111. doi: 10.1021/jo00041a010
- Leyssen P., de Clercq E., Neyts J. // Mol. Pharmacol. 2006. Vol. 69. P. 1461. doi: 10.1124/mol.105.020057
 
				
			 
						 
					 
						 
						 
						

 
  
  
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