| Abstract [eng] |
Pyrazole derivatives can be applied in various fields, such as agriculture, dye industry, optical science, electronics. Nowadays, however, these compounds are commonly used in pharmaceutical industry due to their broad range of biological activity, for example anticancer, antibacterial, antifungal, analgesic, anti-tuberculous, anti-HIV, anti-inflammatory, antipyretic, anticonvulsant, antidepressant, angiotensin converting enzyme (ACE) inhibition, cholecystokinin-1 (CCK-1) receptor antagonists, estrogen receptor (ER) ligands. The aim of this work was to synthesize 3-alkynyl-1-phenyl-1H-pyrazol-4-carbaldehydes from 3-hydroxy-1-phenyl-1H-pyrazole in few steps. 3-alkynyl-1phenyl-1H-pyrazol-4-carbaldehydes were used to obtain 2H-dipyrazolo[1,5-a:4',3'-c]pyridines. First, benzylation of 3-hydroxy-1-phenyl-1H-pyrazole was performed. Then using Vilsmieier-Haack formylation reaction 3-benzyloxy-1-phenyl-1H-pyrazol-4-carbaldehyde was obtained. Afterwards, benzyl group was deprotected to prepare a compound for the following triflate addition. Lastly, Sonogashira cross-coupling reaction was performed resulting in 3-alkynyl-1phenyl-1H-pyrazol-4-carbaldehydes. Afterwards, cascade multicomponent reaction of 3-alkynyl-1-phenyl-1H-pyrazol-4-carbaldehydes was performed afording new polycyclic compounds with 2H-dipyrazolo[1,5-a:4',3'-c]pyridine core. The structures of the resulting compounds were comfirmed by means of MS, NMR, IR spectroscopy. The study of the anticancer activity didn‘t show promising results, however, only two of them exhibited some activity in concentration range of <24μM. Resulting compounds showed good optical properties, later on their structure could be optimized and used in cell visualization field. |
