A method for the synthesis of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine containing fragments of ω-amino acids with different lengths of the polymethylene chain as a linker has been developed. It was found in experiments in vitro that the obtained compounds are active against the herpes simplex virus type 1, including the acyclovir-resistant strain.
Similar content being viewed by others
References
Herpes Simplex Virus; WHO Fact Sheet. https://www.who.int/news-room/fact-sheets/detail/herpes-simplexvirus, 2020.
Suzich, J. B.; Cliffe, A. R. Virology 2018, 522, 81.
Andrei, G.; Georgala, A.; Topalis, D.; Fiten, P.; Aoun, M.; Opdenakker, G.; Snoeck R. J. Infect. Dis. 2013, 207, 1295.
(a) Brady, R. C.; Bernstein, D. I. Antiviral Res. 2004, 61, 73. (b) Kukhanova, M. K.; Korovina, A. N.; Kochetkov, S. N. Biochemistry (Moscow) 2014, 79, 1635. [Usp. Biol. Khimii 2014, 54, 457.]
Piret, J.; Boivin, G. Antimicrob. Agents Chemother. 2011, 55, 459.
(a) Vigorov, A. Yu.; Krasnov, V. P.; Gruzdev, D. A.; Men'shikova, A. A.; Demin, A. M.; Levit, G. L.; Charushin, V. N. Mendeleev Commun. 2014, 24, 35. (b) Gruzdev, D. A.; Musiyak, V. V.; Chulakov, E. N.; Levit, G. L.; Krasnov, V. P. Chem. Heterocycl. Compd. 2015, 51, 738. [Khim. Geterotsikl. Soedin. 2015, 51, 738.] (c) Krasnov, V. P.; Gruzdev, D. A.; Chulakov, E. N.; Vigorov, A. Yu.; Musiyak, V. V.; Matveeva, T. V.; Tumashov, A. A.; Levit, G. L.; Charushin, V. N. Mendeleev Commun. 2015, 25, 412. (d) Eletskaya, B. Z.; Konstantinova, I. D.; Paramonov, A. S.; Esipov, R. S.; Gruzdev, D. A.; Vigorov, A. Yu.; Levit, G. L.; Miroshnikov, A. I.; Krasnov, V. P.; Charushin, V. N. Mendeleev Commun. 2016, 26, 6. (e) Krasnov, V. P.; Vigorov, A. Yu.; Musiyak, V. V.; Nizova, I. A.; Gruzdev, D. A.; Matveeva, T. V.; Levit, G. L.; Kravchenko, M. A.; Skornyakov, S. N.; Bekker, O. B.; Danilenko, V. N.; Charushin, V. N. Bioorg. Med. Chem. Lett. 2016, 26, 2645. (f) Gruzdev, D. A.; Chulakov, E. N.; Levit, G. L.; Kravchenko, M. A.; Krasnov, V. P.; Charushin, V. N. Mendeleev Commun. 2017, 27, 547. (g) Gruzdev, D. A.; Musiyak, V. V.; Levit, G. L.; Krasnov, V. P.; Charushin, V. N. Russ. Chem. Rev. 2018, 87, 604. [Usp. Khim. 2018, 87, 604.] (h) Musiyak, V. V.; Gruzdev, D. A.; Kravchenko, M. A., Vakhrusheva, D. V.; Levit, G. L.; Krasnov, V. P.; Charushin, V. N. Mendeleev Commun. 2019, 29, 11. (i) Krasnov, V. P.; Musiyak, V. V.; Vozdvizhenskaya, O. A.; Galegov, G. A.; Andronova, V. L.; Gruzdev, D. A.; Chulakov, E. N.; Vigorov, A. Yu.; Ezhikova, M. A.; Kodess, M. I.; Levit, G. L.; Charushin, V. N. Eur. J. Org. Chem. 2019, 30, 4811. (j) Krasnov, V. P.; Levit, G. L.; Musiyak, V. V.; Gruzdev, D. A.; Charushin, V. N. Pure Appl. Chem. 2020, 92, 1277.
(a) Kalgutkar, A. S.; Crews, B. C.; Marnett, L. J. J. Med. Chem. 1996, 39, 1692. (b) Haulotte, E.; Laurent, P.; Braekman, J.-C. Eur. J. Org. Chem. 2012, 10, 1907.
(a) Gao, L.; Xia, H.; Wang, X.; Li, L.; Chen, H. Spectrochim. Acta, Part A 2015, 139, 222. (b) Stephens, T. C.; Lodi, M.; Steer, A. M.; Lin, Y.; Gill, M. T.; Unsworth, W. P. Chem.–Eur. J. 2017, 23, 13314.
Cook, E. S.; Fujii, A.; Tanaka, K.; Tsuchiya, Y. J. Med. Chem. 1971, 14, 354.
Guénin, E.; Monteil, N.; Bouchemal, N.; Prangé, T.; Lecouvey, M. Eur. J. Org. Chem. 2007, 20, 3380.
Charushin, V. N.; Gorbunov, E. B.; Rusinov, G. L.; Likholobov, V. A.; Rodionov, V. A. RU Patent 2434005; Chem. Abstr. 2011, 155, 683753.
Zav'yalov, S. I.; Kravchenko, N. E. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 1514. [Izv. Akad. Nauk, Ser. Khim. 1988, 1696.]
Nagasawa, H. T.; Elberling, J. A.; Fraser, P. S.; Mizuno, N. S. J. Med. Chem. 1971, 14, 501.
Ballini, R.; Papa, F.; Abate, C. Eur. J. Org. Chem. 1999, 87.
Itoh, K.; Kori, M.; Inada, Y.; Nishikawa, K.; Kawamatsu, Y.; Sugihara H. Chem. Pharm. Bull. 1986, 34, 2078.
Tomar, R.; Bhattacharya, D.; Arulananda Babu, S. Tetrahedron 2019, 75, 2447.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(4), 490–497
Rights and permissions
About this article
Cite this article
Vozdvizhenskaya, O.А., Andronova, V.L., Galegov, G.А. et al. Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine. Chem Heterocycl Comp 57, 490–497 (2021). https://doi.org/10.1007/s10593-021-02929-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-021-02929-z