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

Authors

  • Tuyet Anh Dang Thi Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000 Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Giang Le-Nhat-Thuy Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000 Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Quynh Giang Nguyen Thi Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000 Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Phuong Hoang Thi Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Anh Nguyen Tuan Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Ha Hoang Mai Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000 Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Thanh Nguyen Ha Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000
  • Tuan Anh Le Faculty of Chemistry, University of Science, Vietnam National University Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi 100000
  • Tuyen Van Nguyen Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000 Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi 100000

DOI:

https://doi.org/10.1007/6024

Keywords:

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

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.

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Published

2021-02-22

Issue

Vol. 57 No. 2 (2021)

Section

Original Papers