Synthesis, Spectral Characterization, and Biological Evaluation of 2-((2-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)hydrazono)methyl)-5-fluorophenol and Its Transition Metal Complexes

25 Jul

Authors: Hanumant Rananaware, M. A. Badgujar

Abstract: A new hydrazone ligand, 2-((2-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)hydrazono)methyl)-5-fluorophenol, was synthesized via the condensation reaction of 5-fluorosalicyldehyde and 7H-pyrrolo[2,3-d]pyrimidine-4-carbaldehyde hydrazone. The ligand was characterized using various spectroscopic techniques, including FTIR, NMR (¹H, ¹³C), UV-Vis, and mass spectrometry, confirming its molecular structure. The ligand was then complexed with several transition metals (Fe²⁺, Cu²⁺, Ni²⁺, Co²⁺) to form metal complexes. The resulting metal complexes were characterized by elemental analysis, FTIR, UV-Vis spectroscopy, and magnetic susceptibility studies. The results indicated that the metal ions coordinated with the ligand via the nitrogen atom of the hydrazone group and the oxygen atom of the phenolic group, forming stable 1:2 complexes with octahedral or square planar geometries, depending on the metal ion. Biological studies of the ligand and its metal complexes demonstrated significant antimicrobial activity against both Gram-positive and Gram-negative bacteria, with the metal complexes showing superior activity compared to the free ligand. In addition, the complexes exhibited notable antioxidant properties, with the Cu²⁺ and Co²⁺ complexes showing the highest scavenging activity. The enhancement of biological activity upon metal coordination suggests that the metal complexes may have potential therapeutic applications as antimicrobial and antioxidant agents. These findings highlight the importance of metal coordination in modulating the biological properties of hydrazone-based ligands, providing a foundation for future studies in medicinal chemistry and bioinorganic chemistry.

DOI: https://doi.org/10.5281/zenodo.21552783