Synthesis and DNase I inhibitory properties of new benzocyclobutane-2,5-diones
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Eight new benzocyclobutane-2,5-diones (1a–1h) were synthesized, and their inhibitory properties against bovine pancreatic DNase I were examined in vitro. Methods & results: Compounds 1a–1h were synthesized using photocycloaddition of duroquinone with various phenyl-substituted ethylenes in the presence of 18W compact fluorescent lamp (visible light). Two compounds, 1,3,4,6-tetramethyl-7- phenylbicyclo[4.2.0]oct-3-ene-2,5-dione (1a) and 1,3,4,6-tetramethyl-7-p-tolylbicyclo[4.2.0]oct-3-ene-2,5- dione (1b) inhibited DNase I in a noncompetitive manner with IC50 values below 150 μM and showed to be more potent DNase I inhibitors than crystal violet, used as a positive control. In order to analyze potential binding sites for the studied compounds with DNase I, molecular docking study was performed. Conclusion: The studied benzocyclobutane-2,5-diones offer a good starting point for a design of new DNase I inhibitors.
Keywords:benzocyclobutane-2,5-diones / DNase I inhibition / Lineweaver–Burk plot / molecular docking / synthesis
Source:Future Medicinal Chemistry, 2019, 11, 18, 2415-
- Future Medicine Ltd.
- Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)
- Obtaining, physicochemical characterization, analysis and biological activity of pharmacologically active compounds (RS-172044)
- Faculty of Medicine of the University of Nis (internal project no. 4)
- Slovenian Research Agency (grant no. P1-0208)