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Exploring Triazole-Connected Steroid-Pyrimidine Hybrids: Synthesis, Spectroscopic Characterization, and Biological Assessment

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Molecules originating from natural sources are physicochemically and biologically diverse. The conjugation of two active biomolecules has become the foundation for medical and pharmaceutical sciences. An effective synthesis of 11 new steroid-pyrimidine conjugates containing 1,2,3-triazole rings was carried out. The group of 3α–OH bile acids (lithocholic, deoxycholic, cholic) and 3β–OH sterols (cholesterol, cholestanol) were respectively modified to azidoacetates. 2-thiouracil was converted into N(1)S and N(3)S dipropargyl derivatives. Azide–alkyne cycloaddition in the presence of copper(I) of the obtained compounds led to the preparation of 1,2,3-triazole derivatives. Based on a series of spectroscopic ( 1 H NMR, 13 C NMR, Fourier-transform infrared (FT-IR)), spectrometric analyses (Electrospray ionization-mass spectrometry (ESI-MS), electron impact-mass spectrometry (EI-MS)), and semiempirical calculations, the structures of all compounds were confirmed. In silico biological tests and molecular docking (for domain 1KZN, 2H94, 5V5Z, 1EZF, 2Q85 ) were performed for selected compounds. The tests performed indicate the theoretical antimicrobial potential of the obtained ligands.

Source: ACS Omega

DOI: 10.1021/acsomega.4c04800

Authors: Anna Kawka, Damian Nowak, Hanna Koenig, Tomasz Pospieszny

Institution: Adam Mickiewicz University in Poznań

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: gold

Estimated APC paid: $1,935