Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones
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. T...
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2025-01-01
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| author | 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 |
| author_facet | 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 |
| author_sort | Oralgazy A. Nurkenov |
| collection | DOAJ |
| description | 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 <sup>1</sup>H NMR spectra for some atoms is a consequence of the existence of four isomers, namely <i>Z</i>-I, <i>Z</i>-II, <i>E</i>-I and <i>E</i>-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 <i>E</i>-isomer equal to 3:2, which coincided with experimental data. We also tested the antibacterial and antifungal activity of the synthesized compounds. |
| format | Article |
| id | doaj-art-6a7dbf2ee7544461814bb150abf3f633 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-6a7dbf2ee7544461814bb150abf3f6332025-01-10T13:19:05ZengMDPI AGMolecules1420-30492025-01-0130116910.3390/molecules30010169Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based HydrazonesOralgazy A. Nurkenov0Anel Z. Mendibayeva1Serik D. Fazylov2Tulegen M. Seilkhanov3Saule K. Kabieva4Ardak K. Syzdykov5Ilya I. Kulakov6Aleksandr V. Iashnikov7Alexey S. Vasilchenko8Larisa E. Alkhimova9Ivan V. Kulakov10Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, KazakhstanInstitute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, KazakhstanInstitute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, KazakhstanLaboratory of Engineering Profile of NMR Spectroscopy, Sh. Ualikhanov Kokshetau University, 76 Abay St., Kokshetau 020000, KazakhstanDepartment of Chemical Technology and Ecology, Karaganda Industrial University, 30 Republic Ave., Temirtau 101400, KazakhstanInstitute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, KazakhstanSchool of Natural Sciences, University of Tyumen, 15a Perekopskaya St., Tyumen 625003, RussiaLaboratory of Antimicrobial Resistance, Institute of Environmental and Agricultural Biology (X-Bio), University of Tyumen, 23 Lenina St., Tyumen 625003, RussiaLaboratory of Antimicrobial Resistance, Institute of Environmental and Agricultural Biology (X-Bio), University of Tyumen, 23 Lenina St., Tyumen 625003, RussiaSchool of Natural Sciences, University of Tyumen, 15a Perekopskaya St., Tyumen 625003, RussiaInstitute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanov St., Karaganda 100008, KazakhstanThe 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 <sup>1</sup>H NMR spectra for some atoms is a consequence of the existence of four isomers, namely <i>Z</i>-I, <i>Z</i>-II, <i>E</i>-I and <i>E</i>-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 <i>E</i>-isomer equal to 3:2, which coincided with experimental data. We also tested the antibacterial and antifungal activity of the synthesized compounds.https://www.mdpi.com/1420-3049/30/1/169nicotinic acidhydrazideshydrazonesNMR spectroscopyDFT calculationsconformational analysis |
| spellingShingle | 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 Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones Molecules nicotinic acid hydrazides hydrazones NMR spectroscopy DFT calculations conformational analysis |
| title | Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones |
| title_full | Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones |
| title_fullStr | Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones |
| title_full_unstemmed | Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones |
| title_short | Synthesis, Structure and Biological Activity of 2-Methyl-5-nitro-6-phenylnicotinohydrazide-Based Hydrazones |
| title_sort | synthesis structure and biological activity of 2 methyl 5 nitro 6 phenylnicotinohydrazide based hydrazones |
| topic | nicotinic acid hydrazides hydrazones NMR spectroscopy DFT calculations conformational analysis |
| url | https://www.mdpi.com/1420-3049/30/1/169 |
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