1,3-Diphenylpyrazoles: synthesis and antiparasitic activities of azomethine derivatives

Rathelot, Pascal; Azas, Nadine; El‐Kashef, Hussein; Delmas, F.; Giorgio, Carole Di; Timon‐David, P.; Maldonado, José; Vanelle, Patrice

doi:10.1016/s0223-5234(02)01388-0

Cited by 184 publications

(75 citation statements)

References 14 publications

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“…1,4-Diphenyl-1H-pyrazole-3-carbaldehyde, 4-(4-fluoroiphenyl)-1-phenyl-1H-pyrazole-3-carbaldehyde 39) and ethyl 2-(8-trifluoromethyl) quinolin-4-ylamino)-benzoate 40) were prepared as reported. All chemicals were obtained from Aldrich, Fluka, or Merck chemicals.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Taher

Khalil

Ahmed

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 2-substituted-1H-benzimidazole derivatives were synthesized and evaluated for antimicrobial, antifungal and cytotoxic activities. The results showed that all tested compounds showed potent antimicrobial activity against some species of Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli, Salmonella typhi) and fungi (Candida albicans) with minimum inhibitory concentrations (MICs) lower than 0.016 µg/mL. In contrast, all tested compounds were inactive against Staphylococcus aureus (Gram-positive bacterium). The final targets were also tested for their antitumor activity in vitro on cervical carcinoma (HeLa) cell line. Eight of the test compounds displayed more potent cytotoxic effect than doxorubicin at nanomolar concentrations. Compounds 2c and 3c exerted the strongest cytoyoxic effect with IC 50 15 and 13 nM, respectively.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Taher

Khalil

Ahmed

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Starting ferrocenyl-(1-phenyl-5-ferrocenyl-3-formylpyrazole [28] 2a, 1-phenyl-5-ferrocenyl-4-formylpyrazole [29] 2b, 1-phenyl-3-ferrocenyl-4-formylpyrazole [30,31] 2c, formylferrocene [32] 2d) and phenylformylpyrazoles (1-phenyl-5-ferrocenyl-4-pyrazolecarboxaldehyde [33] 4a, and 1-phenyl-3-ferrocenyl-4-pyrazolecarboxaldehyde [34] 4b) were obtained by methods described in literature. …”

Section: Methodsmentioning

confidence: 99%

“…Noteworthy, pyrazole motif makes up the core structure of numerous biologically active compounds. [6] Some pyrazole compounds have affinity for the human CRF-1 receptor, [7] exhibit anti-viral/antitumor, [8] antibacterial, [9] anti-parasitic, [10] antipyretic, [11] antyflammatory, [9,11,12] analgesic, [12] fungistatic, [13] fungicidal, [14] and anti-hyperglycemic activity. [15] Ferrocene and porphyrins have already been associated by means of various methods.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Ferrocene-Modified Porphyrins by Reductive Amination Reaction

Osipova¹,

Rodionov²,

Simenel³

et al. 2011

MHC

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“…Besides, pyrazole derivatives have been of great interest in medicinal chemistry for their role as potent antiparasitic [13], antimicrobial [14], and antitumor agents [15]. (4-Chlorophenyl)-[1-(4-nitrophenyl)-3-phenylpyrazol-4-ylmethylene]amine [13] compound possesses a good activity against L. infantum with IC50 of 12.4 M while 5-(3-isobutyl-1-phenyl-1H-pyrazol-4-yl)-2-substituted-1,3,4-oxadiazoles [15] have an anticancer activity against breast and liver cell line with IC50 of around 2-7 M and 4-13 M, respectively.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives

Le¹,

Pham²,

Nguyen³

2018

Journal of Chemistry

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N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes a-c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes d-f were observed as a result. Reactions between the aldehydes a-f and 7-chloro-4-hydrazinylquinoline , obtained from reaction of 4,7-dichloroquinoline and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines a-c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines d-f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1 H, 13 C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, a-c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus niger at the concentration of 25 g/mL and 50 g/mL, respectively, while compound e only shows a cytotoxic activity against Aspergillus niger at the concentration of 25 g/mL.

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1,3-Diphenylpyrazoles: synthesis and antiparasitic activities of azomethine derivatives

Cited by 184 publications

References 14 publications

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Synthesis of Certain 2-Substituted-1<i>H</i>-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents

Synthesis of Ferrocene-Modified Porphyrins by Reductive Amination Reaction

Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives

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