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Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives.


ABSTRACT: In this paper, a series of new substituted-5-pyrazolones were first synthesized, then formulated by the Vilsmeier-Haack reaction to obtain substituted-4-carbaldehyde-5-pyrazolones. In the final step, when urea was reacted with formulated pyrazolones, we found that, instead of the C=N bond in azomethine form, the compounds tautomerized to form a series of novel pyrazole-4-ylidenemethylurea structures. The structures of these compounds were elucidated by FTIR, 1H, 13C NMR, LC-MS/MS, and elemental analysis methods. The cytotoxic and antioxidant effects of substituted 5-pyrazolones and their pyrazolone-urea derivatives were investigated in metastatic A431 and noncancerous HaCaT human keratinocytes by a mitochondrial activity test. The effects of the compounds on the migration of cancerous and noncancerous cell lines were investigated by using a cell scratch assay. The General Linear Model, Statistical Package for Social Sciences (SPSS v26) was used to determine if there was a statistically significant difference between the control and the treatment groups. Four of the nine compounds showed an antioxidant effect. All 5-pyrazolone-urea compounds showed higher toxicity (p < 0.05) in cancerous A431 cells compared to noncancerous cells at all time points. All compounds also showed a biphasic hormetic effect. Four of the nine compounds inhibited cell migration.

SUBMITTER: Gediz Erturk A 

PROVIDER: S-EPMC7070565 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives.

Gediz Erturk Aliye A   Omerustaoglu Hilal H  

Molecules (Basel, Switzerland) 20200218 4


In this paper, a series of new substituted-5-pyrazolones were first synthesized, then formulated by the Vilsmeier-Haack reaction to obtain substituted-4-carbaldehyde-5-pyrazolones. In the final step, when urea was reacted with formulated pyrazolones, we found that, instead of the C=N bond in azomethine form, the compounds tautomerized to form a series of novel pyrazole-4-ylidenemethylurea structures. The structures of these compounds were elucidated by FTIR, <sup>1</sup>H, <sup>13</sup>C NMR, LC  ...[more]

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