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Issue 15, 2017
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Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification

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Abstract

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.

Graphical abstract: Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification

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Publication details

The article was received on 02 May 2017, accepted on 09 Jun 2017 and first published on 12 Jun 2017


Article type: Paper
DOI: 10.1039/C7NJ01469D
Citation: New J. Chem., 2017,41, 7531-7543
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    Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification

    A. Bistrović, N. Stipaničev, T. Opačak-Bernardi, M. Jukić, S. Martinez, Lj. Glavaš-Obrovac and S. Raić-Malić, New J. Chem., 2017, 41, 7531
    DOI: 10.1039/C7NJ01469D

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