Alena Stalinskaya
@utmn.ru
Chemistry
RESEARCH INTERESTS
Heterocyclic compounds, 3-acetyl-2-methylpyridines, chemical modifications, biological activity
Scopus Publications
Scholar Citations
Scholar h-index
Scholar i10-index
Scopus Publications
Alena L. Stalinskaya, Natalia A. Dengis, Vasily S. Vlasenko, and Ivan V. Kulakov
Springer Science and Business Media LLC
Ivan V. Kulakov, Alena L. Stalinskaya, Semyon Y. Chikunov, Irina A. Pustolaikina, and Yuri V. Gatilov
Georg Thieme Verlag KG
AbstractIn this work, the cyclization reactivity of various 3-acetyl-2-methylpyridines (including 3-acetyl-2-methylquinoline) containing both electron donor and acceptor substituents with salicylaldehyde into epoxybenzooxocino[4,3-b]pyridine derivatives was studied. The reactions were carried out in mild (under room temperature or reflux in 2-propanol) and harsh (in a sealed glass ampoule) conditions. It was shown that 3-acetyl-2-methylpyridines with an aryl substituent in the 4-position do not react with salicylaldehyde either under normal convection heating conditions or under more severe conditions. This effect was explained by the steric hindrance of the substituents using quantum chemical calculations. It was found that electron donor substituents in 3-acetyl-2-methylpyridines significantly facilitate cyclization in epoxybenzooxocino[4,3-b]pyridines. The presence of electron acceptor substituents (NO2 group for example) in the 5-position of pyridine prevents cyclization under normal conditions, but gives a rather high conversion to oxocinopyridines under more specific conditions. This effect is quantum-chemically explained by the decrease in the basicity of pyridine. Pyridines with two pairs of methyl groups in ortho-positions to the acetyl group are capable to form mixtures of regioisomeric epoxybenzooxocinopyridines. Further, epoxybenzooxocinopyridines with methyl and acetyl groups can form a mixture of diastereomeric bisoxocins under more specific conditions. All 17 initial pyridines were studied quantum-chemically in order to understand what features of their structure and properties affect the success of the cyclization reaction and the yield of the target product. The pyridine molecules were calculated by the DFT RB3LYP/6-311++G(d,p) method taking into account the alcohol solvent within the CPCM model using Gaussian-2016 program. It was shown that the absence of steric hindrances in the form of bulky substituents in 4-position of pyridines is the main factor affecting the success of the cyclization reaction. Also, the yield of the target product is affected by the CH-acidity of the methyl group in 2-position, which, in turn, is affected by electron-donating and electron-withdrawing substituents in the 5- and 6-positions.
Zarina Shulgau, Alena Stalinskaya, Shynggys Sergazy, Aigerim Zhulikeyeva, Yevgeniy Kamyshanskiy, Alexander Gulyayev, Yerlan Ramankulov, and Ivan Kulakov
Elsevier BV
Alena L. Stalinskaya, Nadezhda V. Martynenko, Larisa E. Alkhimova, Diana S. Dilbaryan, Alexey S. Vasilchenko, Natalia A. Dengis, Vasily S. Vlasenko, and Ivan V. Kulakov
Elsevier BV
Daria M. Turgunalieva, Alena L. Stalinskaya, Ilya I. Kulakov, Galina P. Sagitullina, Victor V. Atuchin, Andrey V. Elyshev, and Ivan V. Kulakov
MDPI AG
The multicomponent reaction of 2-nitroacetophenone (or nitroacetone), acetaldehyde diethyl acetal, β-dicarbonyl compound, and ammonium acetate in an acetic acid solution allowed the acquisition of previously undescribed 4-methyl-substituted derivatives of 5-nitro-1,4-dihydropyridine in satisfactory yields. The oxidation of the obtained 5-nitro-1,4-dihydropyridine derivatives resulted in the corresponding 2,4-dimethyl-5-nitropyridines. In addition, for the first time in the synthesis of unsymmetrical 1,4-dihydropyridines by the Hantzsch reaction acetaldehyde, diethyl acetal was used as a source of acetaldehyde. The use of more volatile and sufficiently reactive acetaldehyde in this reaction did not lead to a controlled synthesis of unsymmetrical 5-nitro-1,4-dihydropyridines. The proposed multicomponent approach to the synthesis of 4-methyl-substituted 5-nitro-1,4-dihydropyridines and their subsequent aromatization into pyridines made it possible to obtain previously undescribed and hardly accessible substituted 5(3)-nitropyridines.
Alena L. Stalinskaya, Nadezhda V. Martynenko, Zarina T. Shulgau, Alexandr V. Shustov, Viktoriya V. Keyer, and Ivan V. Kulakov
MDPI AG
The COVID-19 pandemic is ongoing as of mid-2022 and requires the development of new therapeutic drugs, because the existing clinically approved drugs are limited. In this work, seven derivatives of epoxybenzooxocinopyridine were synthesized and tested for the ability to inhibit the replication of the SARS-CoV-2 virus in cell cultures. Among the described compounds, six were not able to suppress the SARS-CoV-2 virus’ replication. One compound, which is a derivative of epoxybenzooxocinopyridine with an attached side group of 3,4-dihydroquinoxalin-2-one, demonstrated antiviral activity comparable to that of one pharmaceutical drug. The described compound is a prospective lead substance, because the half-maximal effective concentration is 2.23 μg/μL, which is within a pharmacologically achievable range.
A. L. Stalinskaya, S. Y. Chikunov, I. A. Pustolaikina, and I. V. Kulakov
Pleiades Publishing Ltd
A. L. Stalinskaya, Z. T. Shulgau, Sh. D. Sergazy, A. E. Gulyaev, D. M. Turdybekov, K. M. Turdybekov, and I. V. Kulakov
Pleiades Publishing Ltd
Alena L. Stalinskaya, Daria F. Weber, Tulegen M. Seilkhanov, and Ivan V. Kulakov
Springer Science and Business Media LLC
Ivan V. Kulakov, Alena L. Stalinskaya, Semyon Y. Chikunov, and Yuri V. Gatilov
Royal Society of Chemistry (RSC)
The reaction of 3,5-diacetyl-2,6-dimethylpyridine with substituted salicylic aldehydes leads to the formation of the epoxybenzooxocine ring. Oxidation of the methylene group with H2SeO3 opens ways to obtaining structural analogs of natural integrastatins A, B.
Ivan V. Kulakov, Alena L. Oleshchuk, Vladislav A. Koveza, and Irina V. Palamarchuk
Informa UK Limited
Abstract Multicomponent reaction of 2-nitroacetophenone, urotropine (or paraformaldehyde), β-dicarbonyl compound and ammonium acetate afforded five new 4-unsubstituted 5-nitro-6-phenyl-1,4-dihydropyridine derivatives, oxidation of which provided the corresponding 5-nitro-6-phenylpyridines. The proposed approach for the synthesis of 4-unsubstituted 5-nitro-6-phenyl-1,4-dihydropyridines and their subsequent aromatization into pyridines made it possible to reduce the total reaction time by more than 200 times and the overall yield of 5-nitro-6-phenylpyridine by 2 times compared with the known methods. Graphical Abstract
Alena L. Oleshchuk, Zarina T. Shulgau, Tulegen M. Seilkhanov, Alexey S. Vasilchenko, Samat A. Talipov, and Ivan V. Kulakov
Georg Thieme Verlag KG
Claisen condensation reaction of diethyl oxalate with 1-[4-(furan-2-yl)-2-methyl-5-nitro-6-phenylpyridin-3-yl]ethan-1-one afforded (Z)-4-[4-(furan-2-yl)-2-methyl-5-nitro-6-phenylpyridin-3-yl]-2-hydroxy-4-oxobut-2-enoic acid. The latter reacted with various binucleophiles to form the corresponding 3,4-dihydroquinoxaline-2(1H)-one, 3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one, and 1H-pyrazole derivatives. Biological screening of the obtained compounds revealed analgesic and antibacterial activity.
Alena L. Oleshchuk, Anastasiya A. Karbainova, Tatyana N. Krivoruchko, Zarina T. Shulgau, Tulegen M. Seilkhanov, and Ivan V. Kulakov
Springer Science and Business Media LLC