caa a22 4500 467920605 CHVBK 20180406152916.0 cr unu---uuuuu 170328e20061101xx s 000 0 eng 10.1007/s00706-006-0537-6 doi (NATIONALLICENCE)springer-10.1007/s00706-006-0537-6 New 3,4-Annelated Coumarin Derivatives: Synthesis, Antimicrobial Activity, Antioxidant Capacity, and Molecular Modeling [Elektronische Daten] [Niko Radulović, Gordana Stojanović, Rastko Vukićević, Vidoslav Dekić, Biljana Dekić, Radosav Palić] Summary.: The one pot reaction preparation, spectral analysis, and molecular modeling experiments on the new 3,4-annelated coumarin systems with bioactivity associated structural features are described. These provided the insight into the equilibrium of the respective tautomeric forms making possible the reconciliation of previously published spectral data with the structure assignments as well as the correction of erroneously established structures. The synthesized compounds were tested in a standard disk diffusion assay and displayed strong to moderate antimicrobial activity, with a promising new lead prototype compound (7-amino-9-hydroxy-5-oxa-7a,8,11-triazacyclopenta[b]phenanthren-6-one (5)) possessing greater activity that the antibiotics Ampicillin and Nystatin. Antioxidant capacities of the compounds, determined spectrophotometrically using a phosphomolybdenum method, were greater, and in the case of compound 5 four times the activity of α-tocopherol acetate. Springer-Verlag, 2006 Keywords. 3,4-Annelated coumarin systems nationallicence Enamino and imino tautomeric forms nationallicence Antimicrobial activity nationallicence Antioxidant capacity nationallicence One pot synthesis nationallicence Radulović Niko Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, Serbia and Montenegro aut Stojanović Gordana Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, Serbia and Montenegro aut Vukićević Rastko Department of Chemistry, Faculty of Science and Mathematics, University of Kragujevac, Kragujevac, Serbia and Montenegro aut Dekić Vidoslav Department of Chemistry, Faculty of Sciences and Mathematics, University of Priština, Serbia and Montenegro aut Dekić Biljana Department of Chemistry, Faculty of Sciences and Mathematics, University of Priština, Serbia and Montenegro aut Palić Radosav Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, Serbia and Montenegro aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/11(2006-11-01), 1477-1486 0026-9247 137:11<1477 2006 137 706 https://doi.org/10.1007/s00706-006-0537-6 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0537-6 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Radulović Niko Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, Serbia and Montenegro aut NATIONALLICENCE 700 1- Stojanović Gordana Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, Serbia and Montenegro aut NATIONALLICENCE 700 1- Vukićević Rastko Department of Chemistry, Faculty of Science and Mathematics, University of Kragujevac, Kragujevac, Serbia and Montenegro aut NATIONALLICENCE 700 1- Dekić Vidoslav Department of Chemistry, Faculty of Sciences and Mathematics, University of Priština, Serbia and Montenegro aut NATIONALLICENCE 700 1- Dekić Biljana Department of Chemistry, Faculty of Sciences and Mathematics, University of Priština, Serbia and Montenegro aut NATIONALLICENCE 700 1- Palić Radosav Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Niš, Serbia and Montenegro aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/11(2006-11-01), 1477-1486 0026-9247 137:11<1477 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer