Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modificationElectronic supplementary information (ESI) available: Radical scavenging capacity (RSC) of compounds after 30 and 60 min, cyclic voltammograms for 16a-16e, 17a-17e, 18a-18e and 19a-19d, ROS detection of 20d at 10−4 M, 1H and 13C NMR spectra of novel compounds. See DOI: 10.1039/c7nj01469d

• Main Authors: Bistrovi, A, Stipani ev, N, Opa ak-Bernardi, T, Juki, M, Martinez, S, Glavaš-Obrovac, Lj, Rai -Mali, S
• Format: Article
• Language: English
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c7nj01469d

Novel natural coumarin-based umbelliferone, herniarin and esculetin series linked to hydroxy- and methoxy-substituted and non-substituted phenyl rings through a 1,2,3-triazole spacer were provided by environmentally friendly click chemistry under microwave irradiation. The antioxidative activity of the compounds was evaluated by DPPH-scavenging activity and cyclic voltammetry assays. While adjacent 6- and 7-hydroxyl groups in coumarins made a major contribution to antioxidative power and a decrease of ROS production relative to esculetin, a p -methoxy-substituted phenyl moiety had an impact on pronounced and selective antiproliferative activity against chronic leukemia cells in blast crisis (K562) with no significant change in the ROS generation. 6,7-Dihydroxycoumarin can be considered as a promising scaffold with a major contribution to antioxidant potential and, thereby, further structural modification of 6,7-dihydroxycoumarin linked to aryl-1,2,3-triazole may provide a hybrid molecule that may be of interest for potential application to prevent diseases related to the oxidative-stress imbalance. Diverse natural coumarin-based compounds linked to aryl via a 1,2,3-triazole spacer with antiproliferative activity against K562 cells, radical scavenging activity and a decrease of ROS production were provided.