Synthesis, Structure and Molecular Docking of New 4,5-Dihydrothiazole Derivatives Based on 3,5-Dimethylpyrazole and Cytisine and Salsoline Alkaloids
Ibrayev M.K. Nurkenov O.A. Rakhimberlinova Z.B. Takibayeva A.T. Palamarchuk I.V. Turdybekov D.M. Kelmyalene A.A. Kulakov I.V.
November 2022MDPI
Molecules
2022#27Issue 21
The interaction results of 1,2-dibromo-3-isothiocyanatopropane with some pyrazoles as well as cytisine and salsoline alkaloids were presented in this paper. It was shown that the reaction resulted in one one-step and rather mild method for the preparation of the corresponding 1,3-thiazoline bromomethyl derivatives. The yield of this reaction was affected by the presence of a base and an order in which reagents were added. Molecular docking of the synthesized 1,3-thiazoline derivatives for putative antibacterial activity was carried out using the penicillin-binding target protein (PBP4) of the bacteria E. coli “Homo sapiens” and S. aureus “Homo sapiens” as an example. Molecular docking demonstrated that the compounds had insignificant binding energies at the level of selected reference drugs (Cephalotin and Chloramphenicol). The presence of natural alkaloids in the structure of thiazoline derivatives somewhat increased the affinity of these substrates for target proteins selected.
1,2-dibromo-3-isothiocyanatopropane , 3,5-dimethyl-1H-pyrazole , 5-(bromomethyl)-2-(3,5-dimethyl-1H-pyrazol-1-yl)-4,5-dihydrothiazole , allylisothiocyanate , cytisine and salsoline alkaloids , intramolecular heterocyclization
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Department of Chemistry and Chemical Technology, Abylkas Saginov Karaganda Technical University, Ave. Nursultan Nazarbayev, 56, Karaganda, 100027, Kazakhstan
Faculty of Chemistry, Karaganda Buketov University, st. University 28, Karaganda, 100024, Kazakhstan
Institute of Organic Synthesis and Coal Chemistry of Republic of Kazakhstan, Alikhanova 1, Karaganda, 100008, Kazakhstan
Institute of Chemistry, Tyumen State University, 15a Perekopskaya St., Tyumen, 625003, Russian Federation
Department of Chemistry and Chemical Technology
Faculty of Chemistry
Institute of Organic Synthesis and Coal Chemistry of Republic of Kazakhstan
Institute of Chemistry
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