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


Kahriman N., Peker K., Serdaroğlu V., Aydın A., Türkmenoğlu B., Usta A., ...Daha Fazla

TURKISH JOURNAL OF CHEMISTRY, cilt.47, sa.2, ss.476-546, 2023 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 47 Sayı: 2
  • Basım Tarihi: 2023
  • Doi Numarası: 10.55730/1300-0527.3553
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.476-546
  • Anahtar Kelimeler: 2, 4, 6-trisubstituted pyrimidine, N-?-D-glucosides, biological activity, molecular docking, INHIBITION, IDENTIFICATION, DERIVATIVES, ACTIVATION, COMPLEXES, DISCOVERY, BINDING, SERIES
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

In this study, syntheses of new pyrimidine-coupled N-beta-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 beta-anomers. Both tested groups exhibited strong antiproliferative activity (2.29-66.84 mu 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 Delta 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.