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Succinyl and Adipoyl Dihydrazones: A Solid-State, Solution and Antibacterial Study.
- Source :
- Crystals (2073-4352); Aug2022, Vol. 12 Issue 8, p1175, 13p
- Publication Year :
- 2022
-
Abstract
- 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-d<subscript>6</subscript> 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-d<subscript>6</subscript> solution, they adopt several conformations, due to rotations around C<subscript>ar</subscript>–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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 20734352
- Volume :
- 12
- Issue :
- 8
- Database :
- Complementary Index
- Journal :
- Crystals (2073-4352)
- Publication Type :
- Academic Journal
- Accession number :
- 158748951
- Full Text :
- https://doi.org/10.3390/cryst12081175