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Two hydrazones derived from 1‐aryl‐3‐( p ‐substituted phenyl)prop‐2‐en‐1‐one: synthesis, crystal structure, Hirshfeld surface analysis and in vitro biological properties
Author(s) -
Dammene Debbih Ouafa,
Sid Assia,
Bouchene Rafika,
Bouacida Sofiane,
Mazouz Wissam,
Gherraf Noureddine
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618006812
Subject(s) - chemistry , hydrazone , chalcone , crystal structure , single crystal , aryl , condensation reaction , intermolecular force , medicinal chemistry , stereochemistry , crystallography , organic chemistry , molecule , alkyl , catalysis
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, C 22 H 18 N 4 O 4 , ( H1 ), and ( Z )‐1‐[( E )‐3‐(4‐chlorophenyl)‐1‐(naphthalen‐1‐yl)allylidene]‐2‐(2,4‐dinitrophenyl)hydrazine, C 25 H 17 ClN 4 O 4 , ( 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.