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SYNTHESIS OF NOVEL 3-ARYLATED 2-HYDROXY-1,4-NAPHTHOQUINONE DERIVATIVES via MICROWAVE-ASSISTED THREE-COMPONENT DOMINO REACTION AND EVALUATION OF THEIR CYTOTOXIC ACTIVITY

Tuyet Anh Dang Thi, Giang Le-Nhat-Thuy, Quynh Giang Nguyen Thi, Phuong Hoang Thi, Anh Nguyen Tuan, Ha Hoang Mai, Thanh Nguyen Ha, Tuan Anh Le, Tuyen Van Nguyen
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Abstract


Synthesis of novel 3-arylated 2-hydroxy-1,4-naphthoquinone derivatives via microwave-assisted three-component reaction starting from 2-hydroxy-1,4-naphthoquinone, tetronic acid, and various aromatic aldehydes has been described. This multicomponent domino reaction proceeded through the Knoevenagel condensation, Michael addition, deprotonation, and 1,3-H shift steps. Five of the synthesized compounds displayed good cytotoxic activity against two human cancer cell lines, KB and HepG2, with half maximal inhibitory concentration values in a range of 4–20 μM.


Keywords


γ-butyrolactone; 1,4-naphthoquinone; tetronic acid; cytotoxic activity,; microwave irradiation; three-component domino reaction

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