Synthesis of the 3,5-diphenyl-1H-pyrazole and cytogenetic and oxidative alterations after exposure of cultured human whole blood cells

Abstract

The 3,5-diphenyl-1H-pyrazole was obtained by condensation reaction of dibenzoylmethane and thiosemicarbazide in acetic acid under conventional heating and microwave irradiation method. The structure of the 3,5-diphenyl-1H-pyrazole confirmed by IR, ¹H, and ¹³C NMR and X-ray diffraction and the geometry optimization was carried out using density functional theory (DFT) methods at B3LYP/6-31G, 6-31G(d), 6-31G(d, p), 6-311G(d, p), 6-311G(2d, 2p), 6-31+G(d, p), 6-311++G(d, p) levels. In addition, cytotoxic and oxidative effects were investigated in cultured human peripheral blood cells.

Keywords:

• pyrazole
• thiosemicarbazide
• cytotoxic

Public Interest Statement

We have been working on heterocyclic chemistry for the last 20 years. We concentrated more on pyrazole-derived compounds due to interesting activity of analgesic, antipyretic, antihypertensive, anti-inflammatory, pesticides, herbicides, plant growth regulators, and calcium ion modulators.

In the study, we obtained pyrazole compound with conventional heating and microwave irradiation method and characterized on the basis of ¹H NMR, ¹³C NMR, FT-IR, and elemental analysis. Additionally, the structure of 3,5-diphenyl-1H-pyrazole was illuminated with X-ray diffraction and pyrazole compound have been optimized geometrically with density functional theory (DFT) in Gaussian in order to obtain information about the 3D geometries and electronic structures.

The 3,5-diphenyl-1H-pyrazole tested in vitro in order to assess their cytotoxic and pro-oxidant potentials. On the biological properties including tests 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide MTT and Lactate dehydrogenase (LDH) assay, Total antioxidant capacity (TAC) and Total oxidative stress (TOS) levels were performed.

Additional information

Notes on contributors

Esvet Akbas

Our research group has been working on the synthesis of pyrazole, pyrimidine and pyridazinone compounds from the class of heterocyclic compounds, the investigation of advanced step reactions, and the biological activities of these compounds.

We are wondering what the consequences will be if the research reported in this manuscript is to be studied in vivo in the future. If these in vivo tests performed at the advanced stage of the current study are positive, more comprehensive projects and articles can be made accordingly.