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Information × Registration Number 0223U005060, 0123U103123 , R & D reports Title Directed synthesis of new heterocyclic sulfonamides as potential anticancer agents popup.stage_title Head Kachaieva Maryna V., Registration Date 13-12-2023 Organization V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine popup.description2 A new series of N-(4-cyano-1,3-oxazol-5-yl)sulfonamides was synthesized and characterized by IR, NMR spectroscopy, elemental analysis, and chromatography-mass-spectrometry. The anticancer activity of all synthesized compounds was evaluated by the National Cancer Institute (USA) using single-dose (10 µM) and five-dose testing against 60 cancer cell lines. Among them, compounds 2 and 10 (N-(4-cyano-2-phenyl-1,3-oxazol-5-yl)-N,4-dimethyl-benzenesulfonamide and N-(4-cyano-2-(thiophene-2 -yl)-1,3-oxazol-5-yl)-N,4-dimethylbenzenesulfonamide, respectively) showed the highest activity against 60 cancer cell lines in a single-dose screening. Compounds 2 and 10 showed inhibitory activity within the GI50 parameter in five-dose studies. The COMPARE analysis showed that disruption of microtubule formation may be one of the mechanisms of the antitumor effect of the synthesized compounds. The influence of the features of the sulfonamide group in oxazoles on anticancer activity was investigated by comparing structurally similar oxazole derivatives with different configurations of the sulfonamide group. It was established that the acceptor effect of this substituent on the oxazole ring at position 5 plays a decisive role in the level of anticancer activity of oxazole derivatives (derivatives in which the SO2 group is directly connected to the oxazole platform). In contrast to them, the 5-amino-4-cyano-1,3-oxazoles synthesized in this work with a different configuration of the sulfonamide group, where its acceptor effect on the oxazole ring is eliminated, showed a worse overall level of activity, however, we found a pronounced selectivity of the action of the compounds on various cancer panels. The obtained results are fundamental and can be used for the design of new anticancer agents with a selective mechanism of action. Product Description popup.authors Bagreeva Oksana S. Hodyna Diana M. Severin Oleksandr O. popup.nrat_date 2023-12-13 Close