New pyrimidine-N-ß-D-glucosides: synthesis, biological evaluation, and molecular docking investigations

Authors

NURAN KAHRİMAN
KIVANÇ PEKER
VİLDAN SERDAROĞLU
ALİ AYDIN
BURÇİN TÜRKMENOĞLU
ASU USTA
NURETTİN YAYLI

Abstract

In this study, syntheses of new pyrimidine-coupled N-ß-glucosides and tetra-O-acetyl derivatives were carried out. All glycoconjugates were investigated in comparison with known chemotherapeutic agents in terms of their antimicrobial and anticancer functions and DNA/protein binding affinities. Spectral data showed that all glycoside derivatives were obtained by diastereoselectivity as ß-anomers. Both tested groups exhibited strong antiproliferative activity (2.29?66.84 ?g/mL), but some of them had sufficiently ideal % cytotoxicity values (10.01%?16.78%). And also all synthetic compounds exhibited remarkable antibacterial activity against human pathogenic bacteria. Binding of these compounds to CT-DNA resulted in significant changes in spectral properties, consistent with groove binding. Molecular docking studies of some compounds revealed that the docking score, complex energy, and MM-GBSA ?GBind energy values were consistent with the experimental results, which showed that the new compounds were potent chemotherapeutic agents. Overall bioactivity results suggest that these compounds may be candidates as new chemotherapeutic agents and deserve further pharmacological evaluation.

DOI

10.55730/1300-0527.3553

Keywords

2, 4, 6-trisubstituted pyrimidine, N-ß-D-glucosides, biological activity, molecular docking

First Page

476

Last Page

494

Recommended Citation

KAHRİMAN, NURAN; PEKER, KIVANÇ; SERDAROĞLU, VİLDAN; AYDIN, ALİ; TÜRKMENOĞLU, BURÇİN; USTA, ASU; and YAYLI, NURETTİN (2023) "New pyrimidine-N-ß-D-glucosides: synthesis, biological evaluation, and molecular docking investigations," Turkish Journal of Chemistry: Vol. 47: No. 2, Article 16. https://doi.org/10.55730/1300-0527.3553
Available at: https://journals.tubitak.gov.tr/chem/vol47/iss2/16