Synthesis, characterization and antimicrobial evaluation of 1-((5,3-diaryl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one

Sid, Assia; Ziani, Nouara; Demmen-Debbih, Ouafa; Mokhtari, Mahieddine; Lamara, Kaddour

doi:10.5155/eurjchem.4.3.268-271.824

Cited by 5 publications

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“…These applications have been the basis for the synthesis of new hydrazones and prompted us to undertake the present investigation. Initially, we employed aldolic condensation, via a Claisen-Schmidt reaction (Sid et al, 2013), in which substituted benzaldehydes were used to react with enolizable methyl aryl ketones under basic conditions to obtain ,unsaturated carbonyl compounds. Then, the reactivity of the carbonyl group allowed us to carry on addition reactions with 2,4-dinitrophenylhydrazine (Brady's reagent) (Sachin et al, 2012) to obtain their hydrazone derivatives.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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“…They are the main precursors for the synthesis of a wide range of a biologically active heterocyclic compounds such as pyrazoles [1][2][3][4][5], isoxazoles [4,5], oxazines [6], pyrimidines [7,8], thiazine derivatives, and many other heterocycles [9]. Chalcone substructure is also well-known for the biosynthesis of flavonoids and isoflavonoids that have high therapeutic and preventive potential of many diseases [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new 3,5-disubstituted-4,5-dihydro-1H-pyrazole and their carbothioamide derivatives

Ibrahim

2015

Eur. J. Chem.

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A new series of substituted pyrazolines (6-10) were synthesized in moderate to excellent yield by treatment of chalcones (1-5) with hydrazine monohydrate. The carbothioamide compounds (11)(12)(13)(14) were obtained in 65% to quantitative yield by treatment of chalcones (2, 4, and 5) either with thiosemicarbazide or with phenylisothiocyanate. All new compounds were characterized by various spectroscopic methods such as 1 H NMR, 13 C NMR, DEPT, COSY, HSQC spectroscopy, elemental analysis, and high resolution mass spectroscopy. The obtained compounds are currently under biological investigations, and the results will be reported elsewhere. KEYWORDS

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Synthesis, spectroscopic characterization, crystal structure, DFT studies and biological activities of new hydrazone derivative: 1-(2,5-bis((E)-4-isopropylbenzylidene)cyclopentylidene)-2-(2,4-dinitrophenyl) hydrazine

Saouli

Selatnia

Zouchoune

et al. 2020

Journal of Molecular Structure

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Synthesis, characterization and antimicrobial evaluation of 1-((5,3-diaryl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one

Cited by 5 publications

References 40 publications

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

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

Synthesis and characterization of new 3,5-disubstituted-4,5-dihydro-1H-pyrazole and their carbothioamide derivatives

Synthesis, spectroscopic characterization, crystal structure, DFT studies and biological activities of new hydrazone derivative: 1-(2,5-bis((E)-4-isopropylbenzylidene)cyclopentylidene)-2-(2,4-dinitrophenyl) hydrazine

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