1315480-35-3Relevant academic research and scientific papers
Synthesis and cytotoxic evaluation of some substituted 5-pyrazolones and their urea derivatives
Erturk, Aliye Gediz,Omerustaoglu, Hilal
, (2020/02/22)
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-4ylidenemethylurea 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.
New investigation of Vilsmeier-type reaction using pyrazolones with various amides
Huang, Yu-Ying,Kaneko, Kimiyoshi,Takayama, Hiroyuki,Kimura, Masayuki,Wong, Fung Fuh
supporting information; experimental part, p. 3786 - 3792 (2011/08/06)
New investigation of Vilsmeier-type reaction was evaluated to realize the solvent effect by using pyrazolones to react with various of amides, including formamide, N-methylformamide, N-propylformamide, N-tert-butylformamide, N,N-dimethylformamide (DMF), N,N-diethylformamide (DEF), N,N-dipropylformamide (DPF), N,N-diisopropylformamide, N,N-dibutylformamide, piperidine-1- carbaldehyde, and pyrrolidine-1-carbaldehyde, in the presence of phosphorous oxychloride POCl3. The unexpected resulting products were observed in this work according to the difference chemoseletivities of substituted amides. The plausible reactive pathways were proposed to explain the experimental result. Crown Copyright
