We have obtained the Fourier transform IR spectra of solutions of benzaldehyde derivatives having different antiviral activities against a herpes virus. We observe a correlation between the presence of hydrogen bonds in the benzaldehyde molecules and the appearance of antiviral properties in the compounds. For compounds having antiviral activity, we have obtained spectral data suggesting the existence of hydrogen bonds of the type C=O⋅⋅⋅H–O and O–H⋅⋅⋅O in the molecules. When the hydrogen atom in the hydroxyl groups are replaced by a methyl group, no intramolecular hydrogen bonds are formed and the compounds lose their antiviral activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press (1999).
T. Ohta, M. Watanabe, K. Watanabe, Y. Shirasu, and T. Kada, Food Chem. Toxicol., 24, No. 51, 54–61 (1986).
H. P. Vasantha Rupasinghe, J. Boutler-Bitzer, T. Ahn, and J. A. Odumeru, Food Res. Int., 39, 575–580 (2006).
A. R. Figueiredo, F. Campos, V. Feitas, and T. Hogg, Food Microbiol., 25, 105–112 (2008).
M. A. Harish Nayaka, U. V. Sathisha, and S. M. Dharmesh, Food Chem., 119, 1307–1312 (2010).
Z. Zhou, Y. Liu, A.-D. Miao, and Sh.-Q. Wang, Europ. J. Pharmacol., No. 13, 1–8 (2005).
Z. Zhou, Y. Zhang, X.-R. Ding, S.-H. Chen, J. Yang, X.-J. Wang, G.-L. Jia, H.-Sh. Chen, X.-Ch. Boa, and Sh.- Q. Wang, Antiviral Res., No. 74, 59–64 (2007).
M. V. Belkov, 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).
G. B. Tolstorozhev, M. V. Belkov, I. V. Skornyakov, G. I. Polozov, V. L. Sorokin, G. A. Ksendzova, and O. I. Shadyro, Nonlinear Phenom. Complex Systems, 14, No. 3, 282–289 (2011).
M. V. Belkov, G. A. Ksendzova, T. F. Raichenok, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 78, No. 1, 5–10 (2011).
M. V. Belkov, 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).
M. V. Belkov, G. I. Polozov, I. V. Skornyakov, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 78, No. 3, 427–432 (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. 2, 248–257 (2012).
O. I. Shadyro, S. N. Samovich, S. D. Brinkevich, E. I. Boreko, O. V. Savinova, and N. I. Pavlova, "Viral replication inhibitors for herpes virus in cell culture," Belarus Patent Application a20110727 (2011).
R. M. Silverstein, D. J. Webster, and D. J. Kiemle, Spectrometric Identification of Organic Compounds, Wiley, New York (2005).
J. W. Robinson, E. M. Skelly Frame, and G. M. Frame II, Undergraduate Instrumental Analysis, Marcel Dekker, New York (2005).
E. Pretsch, P. Bühlmann, and C. Affolter, Structure Determination of Organic Compounds [Russian translation], Mir, Moscow (2006).
M. V. Belkov, S. D. Brinkevich, S. N. Samovich, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, and O. I. Shadyro, Zh. Prikl. Spektrosk., 78, No. 6, 851–858 (2011).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 79, No. 4, pp. 658–663, July–August, 2012.
Rights and permissions
About this article
Cite this article
Tolstorozhev, G.B., Skornyakov, I.V., Belkov, M.V. et al. Hydrogen bonds and antiviral activity of benzaldehyde derivatives. J Appl Spectrosc 79, 645–650 (2012). https://doi.org/10.1007/s10812-012-9652-9
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10812-012-9652-9