Syntheses, crystal structures, theoretical insights and DNA (1BNA) docking studies of 3-(3-oxo-1,3-dihydroisobenzofuran-1-yl)aminobenzoic acid and its metal complexes
Inorganica Chimica Acta, cilt.596, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 596
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.ica.2026.123137
- Dergi Adı: Inorganica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex
- Anahtar Kelimeler: Co(II) complex, Crystal structure, DFT, Isobenzofuranone derivatives, Molecular docking, Zn(II) complex
- Hacettepe Üniversitesi Adresli: Evet
Özet
In this study, a new organic ligand derived from 3-(3-oxo-1,3-dihydroisobenzofuran-1-yl)aminobenzoic acid (1) and its Zn(II) (2) and Co(II) (3) complexes were synthesized. The structures of the synthesized compounds were comprehensively characterized by elemental analysis, NMR, FT-IR and UV–Vis spectroscopies and single crystal X-ray diffraction. The electronic properties, frontier orbital distributions, enhanced stabilities and charge transfer tendencies of the synthesized ligand and compounds were clarified by the DFT studies. Single crystal X-ray diffraction analyses showed that the asymmetric units of the complexes were containing only one molecule with the different coordination environments shaped by the steric and electronic contributions of the auxiliary ligands. FT-IR data indicated that both the carbonyl and amino groups play active roles in the coordination of the ligand, as confirmed by the appearance of characteristic shifts in the metal complexes. In the UV–Vis spectra, bands attributed to π → π* and/or n → π* transitions were observed in the range of 320–335 nm, and the d–d transition observed in the Co(II) complex around 515 nm was found to be consistent with the octahedral Co(II) centers reported in the literature. Molecular docking studies showed that the ligands and complexes exhibited significant binding with the DNA (1BNA) double helix via hydrogen bonds and hydrophobic interactions. The binding scores of the complexes were found to be higher than those of the free ligand in terms of DNA interaction capacity, suggesting that metalation may increase biological activity. Hirshfeld surface analyses, besides interaction energy calculations and energy frameworks, demonstrated that O–H···O and N–H···O hydrogen bonds contribute significantly to bond stabilizations. Overall, the findings highlight that new 3-aminobenzoic acid–based ligand systems represent promising candidates in both coordination chemistry and drug design.