Naslov
Succinyl and adipoyl dihydrazones: a solid-state, solution and antibacterial study
(Succinyl and adipoyl dihydrazones: a solid-state, solution and antibacterial study)

Autori
Topić, Edi ; Damjanović, Vladimir ; Pičuljan, Katarina ; Vrdoljak, Višnja ; Rubčić, Mirta

Izvornik
Crystals (2073-4352) 12 (2022), 8; 1175, 13

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
hydrazones ; tautomerism ; structural analysis ; NMR spectroscopy ; antibacterial activity

Sažetak
A series of aryl-functionalized alkyl dihydrazones was prepared by condensation of succinyl or adipoyl dihydrazide and selected ortho- hydroxybenzaldehydes (2-hydroxybenzaldehyde, 2- hydroxy-1-naphthaldehyde, 2, 3- dihydroxybenzaldehyde, and 2, 4- dihydroxybenzaldehyde) in solution. The obtained products were structurally characterized in the solid state by single-crystal X-ray diffraction (SC-XRD), thermal analysis (TGA-DSC), and Fourier transform infrared (FTIR) spectroscopy and in DMSO-d6 solution by nuclear magnetic resonance (NMR) techniques. Combined FTIR and crystal structure data point to a N–NH–C=O tautomeric form of the hydrazone parts as well as the enol-imino tautomeric form of the aldehyde residues and a robust trans-syn conformation for the structurally investigated ones. While the molecules retain the same tautomeric form in the DMSO-d6 solution, they adopt several conformations, due to rotations around Car–C, C–N, and N–N bonds. The compounds show exceptional thermal stability, with a complex degradation pattern. Slight differences in thermal behavior correlate to alkyl chain length and aryl substituents. The in vitro cytotoxic activity of prepared dihydrazones was evaluated on THP-1 and HepG2 cell lines, while their antibacterial activity was tested against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Moraxella catarrhalis bacteria. All compounds proved to be non-cytotoxic, and some exhibited moderate antibacterial activity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA