Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis, Structure and Molecular Docking of New 4,5-Dihydrothiazole Derivatives Based on 3,5-Dimethylpyrazole and Cytisine and Salsoline Alkaloids

Version 1 : Received: 25 October 2022 / Approved: 26 October 2022 / Online: 26 October 2022 (09:53:38 CEST)

A peer-reviewed article of this Preprint also exists.

Ibrayev, M.K.; Nurkenov, O.A.; Rakhimberlinova, Z.B.; Takibayeva, A.T.; Palamarchuk, I.V.; Turdybekov, D.M.; Kelmyalene, A.A.; Kulakov, I.V. Synthesis, Structure and Molecular Docking of New 4,5-Dihydrothiazole Derivatives Based on 3,5-Dimethylpyrazole and Cytisine and Salsoline Alkaloids. Molecules 2022, 27, 7598. Ibrayev, M.K.; Nurkenov, O.A.; Rakhimberlinova, Z.B.; Takibayeva, A.T.; Palamarchuk, I.V.; Turdybekov, D.M.; Kelmyalene, A.A.; Kulakov, I.V. Synthesis, Structure and Molecular Docking of New 4,5-Dihydrothiazole Derivatives Based on 3,5-Dimethylpyrazole and Cytisine and Salsoline Alkaloids. Molecules 2022, 27, 7598.

Abstract

In this paper, we present the interaction results of 1,2-dibromo-3-isothiocyanatopropane with some pyrazoles and cytisine and salsoline alkaloids. It has been shown that the reaction results in the one-step and rather mild method for the preparation of the corresponding 1,3-thiazoline bromomethyl derivatives. The yield of this reaction is affected by the presence of a base and the order in which the reagents are added. Molecular docking of the synthesized 1,3-thiazoline derivatives for putative antibacterial activity has been 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 shows that the compounds have 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 increases the affinity of these substrates for target proteins selected.

Keywords

allylisothiocyanate; 1,2-dibromo-3-isothiocyanatopropane; 3,5-dimethyl-1H-pyrazole; intramolecular heterocyclization; 5-(bromomethyl)-2-(3,5-dimethyl-1H-pyrazol-1-yl)-4,5-dihydrothiazole; alkaloid cytisine; alkaloid salsoline

Subject

Chemistry and Materials Science, Organic Chemistry

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