Synthesis and Cytotoxicity of bis(pyrazol-1-yl)-Alkane Derivatives with Polymethylene Linkers and Related Mono- and Dipyrazolium Salts
- Zatonskaya, Lina V [ II Polzunov Altai State Tech Univ, 46 Lenina Ave, Barnaul 656038, Russia ]
- Schepetkin, Igor A [ Montana State University: Microbiology & Cell Biology ] [ Tomsk Polytech Univ, RASA Ctr Tomsk, 30 Lenina Ave, Tomsk 634050, Russia ]
- Petrenko, Tatiana V [ Russian Acad Sci, Inst Petr Chem, Siberian Branch, 4 Akad Skii Ave, Tomsk 634055, Russia ]
- Ogorodnikov, Vladimir D [ Russian Acad Sci, Inst Petr Chem, Siberian Branch, 4 Akad Skii Ave, Tomsk 634055, Russia ]
- Khlebnikov, Andrei I [ II Polzunov Altai State Tech Univ, 46 Lenina Ave, Barnaul 656038, Russia ] [ Natl Res Tomsk Polytech Univ, 30 Lenina Ave, Tomsk 634050, Russia ]
- Potapov, Andrei S [ II Polzunov Altai State Tech Univ, 46 Lenina Ave, Barnaul 656038, Russia ] [ Natl Res Tomsk Polytech Univ, 30 Lenina Ave, Tomsk 634050, Russia ]
Reactions of alpha,omega-dibromoalkanes with pyrazole and 3,5-dimethylpyrazole in superbasic medium of dimethyl sulfoxide - potassium hydroxide were used for the synthesis of bidentate ligands: bis(pyrazol-1-yl)alkanes and bis(3,5-dimethylpyrazol-1-yl)alkanes linked by alkyl chains containing between four and twelve methylene groups. Oxidative iodination of the obtained compounds with I2-HIO3-H2SO4 system in acetic acid provided diiodo derivatives: bis(4-iodopyrazol-1-yl)alkanes and bis(4-iodo-3,5-dimethylpyrazol-1-yl)alkanes. The obtained diiodo derivatives of pyrazole were further converted to mono- and dipyrazolium salts by alkylation of nitrogen atom at position 2 of the pyrazole rings with iodomethane, as well as with methyl triflate. These products are of interest as precursors to mesoionic N-heterocyclic carbene complexes. The cytotoxicity of the obtained compounds was studied against THP-1 monocytic leukemia cells.