Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/4/900 |
| _version_ | 1828425419295031296 |
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| author | Aliye Gediz Erturk Hilal Omerustaoglu |
| author_facet | Aliye Gediz Erturk Hilal Omerustaoglu |
| author_sort | Aliye Gediz Erturk |
| collection | DOAJ |
| description | 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-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 (<i>p</i> < 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. |
| first_indexed | 2024-12-10T16:30:19Z |
| format | Article |
| id | doaj.art-5a4170b52c45479ab629c115726100f6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T16:30:19Z |
| publishDate | 2020-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5a4170b52c45479ab629c115726100f62022-12-22T01:41:33ZengMDPI AGMolecules1420-30492020-02-0125490010.3390/molecules25040900molecules25040900Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea DerivativesAliye Gediz Erturk0Hilal Omerustaoglu1Department of Chemistry, Faculty of Science & Arts, Ordu University, 52200 Ordu, TurkeyDepartment of Chemistry, Faculty of Science & Arts, Ordu University, 52200 Ordu, TurkeyIn 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-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 (<i>p</i> < 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.https://www.mdpi.com/1420-3049/25/4/9005-pyrazoloneurea derivativescell proliferationantioxidant activity |
| spellingShingle | Aliye Gediz Erturk Hilal Omerustaoglu Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives Molecules 5-pyrazolone urea derivatives cell proliferation antioxidant activity |
| title | Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives |
| title_full | Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives |
| title_fullStr | Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives |
| title_full_unstemmed | Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives |
| title_short | Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives |
| title_sort | synthesis and cytotoxic evaluation of some substituted 5 pyrazolones and their urea derivatives |
| topic | 5-pyrazolone urea derivatives cell proliferation antioxidant activity |
| url | https://www.mdpi.com/1420-3049/25/4/900 |
| work_keys_str_mv | AT aliyegedizerturk synthesisandcytotoxicevaluationofsomesubstituted5pyrazolonesandtheirureaderivatives AT hilalomerustaoglu synthesisandcytotoxicevaluationofsomesubstituted5pyrazolonesandtheirureaderivatives |