Antimony(III) complexes with 2-amino-4,6-dimethoxypyrimidines: Synthesis, characterization and biological evaluation

TUNÇ T., KARACAN M. S., Ertabaklar H., SARI M., KARACAN N., Buyukgungor O.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, vol.153, pp.206-214, 2015 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 153
  • Publication Date: 2015
  • Doi Number: 10.1016/j.jphotobiol.2015.09.022
  • Journal Name: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.206-214
  • Keywords: Antimony(III) complexes, Antileishmanial activity, Glutathione reductase inhibition, GLUTATHIONE-REDUCTASE INHIBITORS, PYRIMIDINE-DERIVATIVES, IN-VITRO, ANTIMALARIAL ACTIVITY, TRANSITION, 2-ACETYLPYRIDINE, ANTIBACTERIAL, HYBRIDS, DESIGN
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

Novel pyrimidine compound bearing disulfide bridge, 5,5'-disulfanediyIbis(2-amino-4,6-dimetoxypyrimidine) (3) was synthesized by reduction of 2-amino-4,6-dimethoxy-5-thiocyanatopyrimidine for the first time, and its structure was confirmed by X-ray crystallographic analysis. Novel binuclear antimony(III) compound of (3), {Sb[5,5'-disulfanediylbis(2-amino-4,6-dimetoxypyrimidine)]Cl-3}(2) (4) and mononuclear antimony(III) compounds, SbL2O3, [L: 2-amino-5-thioI-4,6-dimethoxy pyrimidine (2) and 2-amino-5-(1H-tetrazol-5-ylthio)-4,6-dimethoxypyrimidine (6)] were synthesized and characterized with the help of elemental analysis, molecular conductivity, FT-IR,H-1-NMR and LC-MS techniques. The geometrical structures optimized by a DFT/B3LYP/LANL2DZ method of the compounds, indicated that monomeric compounds have square pyramidal shape. Both antileishmanial activity against Leishmania tropica promastigote and glutathione reductase inhibitory activity were determined in vitro. The results showed that (3) has the best biological activity. (C) 2015 Elsevier B.V. All rights reserved.