Two hydrazones derived from 1-aryl-3-(p-substituted phenyl)prop-2-en-1-one: synthesis, crystal structure, Hirshfeld surface analysis andin vitrobiological properties

Abstract

Two chalcones were synthesized by the aldolic condensation of enolizable aromatic ketones with substituted benzaldehydes under Claisen-Schmidt reaction conditions and then treated with 2,4-dinitrophenylhydrazine to yield their corresponding hydrazones. The two (E,Z)-2,4-dinitrophenylhydrazone structures, namely (Z)-1-(2,4-dinitrophenyl)-2-[(E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine, CHNO, (H1), and (Z)-1-[(E)-3-(4-chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine, CHClNO, (H2), were isolated by recrystallization and characterized by FT-IR, UV-Vis, single-crystal and powder X-ray diffraction methods. The UV-Vis spectra of the hydrazones have been studied in two organic solvents of different polarity. It was found that (H2) has a molar extinction coefficient larger than 40000. Single-crystal X-ray diffraction analysis reveals that the molecular zigzag chains of (H1) and (H2) are interconnected through noncovalent contacts. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. All the synthesized chalcones and hydrazones were evaluated for their antibacterial and antioxidant activities. Results indicate that the studied compounds show significant activity against Gram negative Escherichia coli strain and the chalcone 3-(4-methylphenyl)-1-phenylprop-2-en-1-one, (C1), was the most effective. In addition, only hydrazone (H1) displayed a moderate DPPH (2,2-diphenyl-1-picryl hydrazyl) scavenging efficiency.

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

“…Formation of pyrazolines 4a , b and 5a , b can be rationalized on the basis of the reaction pathway. Firstly, formation of hydrazone intermediate followed by subsequent addition of N‐H proton to benzylidene bond moiety followed by ring closure [38, 40, 41], to give the dihydropyrazolines 5a and 5b as final products. While in the case of pyrazolines 4a and 4b the reaction took place through the forming of the dihydropyrazolines intermediate which underwent autoxidation by the loss of hydrogen molecule with the formation of 4a and 4b (Figure 2).…”

Synthesis of a new diarylhydrazone derivative and an evaluation of its in vitro biofilm inhibition and quorum sensing disruption along with a molecular docking study

“…The new diarylhydrazone 6 was successfully synthesized in good yields from 2,4-dinitrophenylhydrazine 5 and an aromatic aldehyde 4 according to literature. [39][40][41][42] The reaction pathway is shown on Scheme 1 and the spectral data HRMS, IR, 1 H NMR, 13 C NMR, and 2D NMR are used for the structural elucidation. All spectra are provided in the Supporting Information.…”