Bioactive carbonyl- and sulfonyl-derivatives of aminophenols were studied. The proton-acceptor abilities of the aminophenols were estimated using a molecular electrostatic potential method. IR Fourier spectra of the aminophenols with different substituents on the amine were measured in solutions and crystals. Molecular functional groups that participate in the formation of H-bonds of the O–H⋯O=C, N–H⋯O=C, O–H⋯O=S=O, and N–H⋯O=S=O types were identified. The aminophenol antiviral activity correlated with the ability to form the H-bonds. A correspondence between the proton-acceptor properties of the hydroxyl oxygen in the aminophenols and their antiviral activity was revealed.
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O. T. Andreeva, L. N. Dunets, P. T. Petrov, O. I. Shadyro, and V. M. Tsarenkov, "Antiviral agent for treating infections caused by Herpes simplex virus" [in Russian], RB Pat. No. 6503 (2004).
O. T. Andreeva, L. N. Dunets, P. T. Petrov, O. I. Shadyro, and V. M. Tsarenkov, "Agent against Herpes" [in Russian], RB Pat. No. 6594 (2004).
O. I. Shadyro, G. A. Ksendzova, G. I. Polozov, V. L. Sorokin, E. I. Boreko, O. V. Savinova, B. V. Dubovik, and N. A. Bizunok, Bioorg. Med. Chem. Lett., 18, No. 7, 2420–2423 (2008).
O. I. Shadyro, G. A. Ksendzova, G. I. Polozov, and V. L. Sorokin, in: Collection of Articles Chemical Problems of Creating New Materials and Technologies [in Russian], NII FKhP BGU, Minsk (2008), pp. 246–257.
E. L. Gasich, V. F. Eremin, G. A. Ksendzova, G. I. Polozov, V. L. Sorokin, and O. I. Shadyro, "Agent for suppressing HIV in cell culture" [in Russian], RB Pat. No. 11933 (2009).
G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, O. I. Shadyro, and A. A. Yakunin, Opt. Spektrosk., 102, No. 4, 602–607 (2007).
M. V. Bel’kov, G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 74, No. 3, 434–439 (2009).
O. K. Bazyl’, V. Ya. Artyukhov, G. V. Maier, T. F. Raichenko, I. V. Skornyakov, G. B. Tolstorozhev, O. I. Shadyro, V. L. Sorokin, and G. A. Ksendzova, Opt. Spektrosk., 107, No. 4, 595–605 (2009).
O. I. Shadyro, V. L. Sorokin, G. A. Ksendzova, G. I. Polozov, S. N. Nikolaeva, N. I. Pavlova, O. V. Savinova, and E. N. Boreko, Khim.-Farm. Zh., 36, No. 8, 14–16 (2002).
O. I. Shadyro, V. L. Sorokin, G. A. Ksendzova, G. I. Polozov, S. N. Nikolaeva, N. I. Pavlova, O. V. Savicheva, and E. N. Boreko, Khim.-Farm. Zh., 37, No. 8, 5–7 (2003).
G. V. Maier, V. Ya. Artyukhov, O. K. Bazyl’, T. N. Kopylova, R. T. Kuznetsova, N. R. Rib, and I. V. Sokolova, Electronically Excited States and Photochemistry of Organic Compounds [in Russian], Nauka, Novosibirsk (1997).
V. Ya. Artyukhov and A. I. Galeeva, Izv. Vyssh. Uchebn. Zaved., Fiz., No. 11, 96–101 (1986).
M. V. Bel’kov, G. A. Ksendzova, P. V. Kuzovkov, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 74, No. 5, 577–582 (2007).
M. V. Bel’kov, A. N. Gorbacheva, G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 77, No. 1, 45–52 (2010).
M. V. Bel’kov, A. N. Gorbacheva, G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 77, No. 3, 340–346 (2010).
M. V. Bel’kov, G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tostorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 77, No. 4, 535–541 (2010).
M. V. Bel’kov, G. A. Ksendzova, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 78, No. 2, 215–221 (2011).
O. K. Bazyl’, V. Ya. Artyukhov, and G. V. Maier, Izv. Vyssh. Uchebn. Zaved., Fiz., 54, No. 6, 3–10 (2011).
O. K. Bazyl’, V. Ya. Artyukhov, G. V. Maier, G. B. Tolstorozhev, T. F. Raichenok, I. V. Skornyakov, O. I. Shadyro, V. L. Sorokin, and G. A. Ksendzova, Opt. Spektrosk., 112, No. 1, 60–69 (2012).
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Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 79, No. 4, pp. 701–708, July–August, 2012.
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Bazyl’, O.K., Artyukhov, V.Y., Mayer, G.V. et al. Quantum-chemical and ir spectroscopic analysis of aminophenol derivatives with antiviral activity. J Appl Spectrosc 79, 687–694 (2012). https://doi.org/10.1007/s10812-012-9658-3
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DOI: https://doi.org/10.1007/s10812-012-9658-3