Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones
Oralgazy A. Nurkenov,
Anel Z. Mendibayeva,
Serik D. Fazylov,
Tulegen M. Seilkhanov,
Saule K. Kabieva,
Ardak K. Syzdykov,
Ilya I. Kulakov,
Aleksandr V. Iashnikov,
Alexey S. Vasilchenko,
Larisa E. Alkhimova,
Ivan V. Kulakov
Affiliations
Oralgazy A. Nurkenov
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, Kazakhstan
Anel Z. Mendibayeva
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, Kazakhstan
Serik D. Fazylov
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, Kazakhstan
Tulegen M. Seilkhanov
Laboratory of Engineering Profile of NMR Spectroscopy, Sh. Ualikhanov Kokshetau University, 76 Abay St., Kokshetau 020000, Kazakhstan
Saule K. Kabieva
Department of Chemical Technology and Ecology, Karaganda Industrial University, 30 Republic Ave., Temirtau 101400, Kazakhstan
Ardak K. Syzdykov
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, Kazakhstan
Ilya I. Kulakov
School of Natural Sciences, University of Tyumen, 15a Perekopskaya St., Tyumen 625003, Russia
Aleksandr V. Iashnikov
Laboratory of Antimicrobial Resistance, Institute of Environmental and Agricultural Biology (X-Bio), University of Tyumen, 23 Lenina St., Tyumen 625003, Russia
Alexey S. Vasilchenko
Laboratory of Antimicrobial Resistance, Institute of Environmental and Agricultural Biology (X-Bio), University of Tyumen, 23 Lenina St., Tyumen 625003, Russia
Larisa E. Alkhimova
School of Natural Sciences, University of Tyumen, 15a Perekopskaya St., Tyumen 625003, Russia
Ivan V. Kulakov
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, Kazakhstan
The synthetic availability and wide range of biological activity of hydrazides and hydrazones make them attractive subjects for investigation. In this study, we focused on synthesis of 2-methyl-5-nitro-6-phenylnicotinohydrazide-based hydrazones derived from the corresponding substituted aldehydes. The structure of the obtained compounds was studied using NMR spectroscopy and DFT calculations. After repeated recrystallization, all the synthesized compounds remained as mixtures of isomers. As a result of a detailed analysis, we found that the duplication and bifurcation of signals in the 1H NMR spectra for some atoms is a consequence of the existence of four isomers, namely Z-I, Z-II, E-I and E-II. Duplicate proton signals with a chemical shift difference of 0.1–0.2 ppm and in a ratio of about 2:1 were noticed in the experimental data. By modeling the structures of individual configurations and conformations, Gibbs free energy values were obtained, which allowed us to estimate the approximate content of rotamers for the E-isomer equal to 3:2, which coincided with experimental data. We also tested the antibacterial and antifungal activity of the synthesized compounds.
