Synthesis, crystal structure, and in silico molecular docking studies of 4-hydroxy-3,5-dimethoxybenzaldehyde (6-chloropyridazin-3-yl)hydrazone monohydrate
Year: 2025
Type: article
Abstract: In the title compound, C 13 H 13 ClN 4 O 3 ·H 2 O, the organic molecule has an E configuration with regard to the C=N bond of the hydrazone bridge. The phenyl and pyridazine rings subtend a dihedral angle of 2.1 (1)° between their mean planes, while the hydrazone moiety makes dihedral angles of 1.6 (2) and 3.0 (2)°, respectively, with these aromatic rings. This renders the entire molecule comparably flat. A C—H...N hydrogen bond generates an inversion dimer with a large R 2 2 (14) ring motif. Within this ring, a further C—H...N hydrogen bond establishes a smaller R 2 2 (8) ring. The molecules of a dimer are thereby firmly linked by four hydrogen bonds. A bifurcated O—H...(O,O) hydrogen bond is formed between a water hydrogen atom and the hydroxyl and methoxy oxygen atoms of an adjacent molecule, leading to the formation of an R 2 1 (5) membered ring. C—H...π and face-to-face π–π stacking interactions are also present in the two-dimensional framework, which may be of relevance for the packing. In a complementary analysis, the compound was docked in silico to EGFR and HER2 receptors and the results imply that the compound targets EGFR preferentially over HER2.
Institution: University of Madras
Language: English
Subfield: Inorganic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $500
OpenAlex ID: W4408834384