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Research ArticleExperimental Studies

Synthesis of Polymethoxylated 3-Styrylflavones and their Antiproliferative Activity in HL60 Cells

ARISA TSUTSUMI, SATORU KAWAII and YUKO YOSHIZAWA
Anticancer Research February 2025, 45 (2) 457-464; DOI: https://doi.org/10.21873/anticanres.17435
ARISA TSUTSUMI
1Laboratory of Bio-organic Chemistry, Tokyo Denki University, Hatoyama, Japan
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SATORU KAWAII
1Laboratory of Bio-organic Chemistry, Tokyo Denki University, Hatoyama, Japan
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  • For correspondence: kawaii@mail.dendai.ac.jp
YUKO YOSHIZAWA
2Laboratory of Bio-organic Chemistry, Akita Prefectural University, Akita, Japan
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Abstract

Background/Aim: Flavonoids are a large group of naturally occurring compounds with a wide range of biological properties and thus they represent a privileged scaffold in medicinal chemistry. We designed and synthesized a series of polymethoxylated 3-styrylflavones as a novel class of styryl-bearing flavone compounds. Materials and Methods: 3-Styrylflavones were systematically synthesized using Wittig reaction between various benzaldehyde derivatives and polymethoxylated 3-(bromomethyl)flavones, and evaluated their antiproliferative activity against HL60. Results: Among the compounds synthesized, 2′,3′,4′-trimethoxy-3-(E)-styrylflavone (IC50=68 μM) and 2′,3′,3‴,4′,4‴,5‴-hexamethoxy-3-(E)-styrylflavone (IC50=92 μM) demonstrated potent anti-proliferative activity. Conclusion: Introduction of 3-styryl substituent in 3-methylflavone increased the antiproliferative activity. Structure-activity relationship studies and theoretical calculations indicated the importance of 2′,3′,4′-trimethoxy-phenyl substituent in enhancing the activity.

Key Words:
  • 3-styrylflavone
  • styryl-flavone hybrid molecule
  • Wittig reaction
  • antiproliferative activity
  • HL60 cells
  • Received December 20, 2024.
  • Revision received January 7, 2025.
  • Accepted January 14, 2025.
  • Copyright © 2025 International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.
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Anticancer Research: 45 (2)
Anticancer Research
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February 2025
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Synthesis of Polymethoxylated 3-Styrylflavones and their Antiproliferative Activity in HL60 Cells
ARISA TSUTSUMI, SATORU KAWAII, YUKO YOSHIZAWA
Anticancer Research Feb 2025, 45 (2) 457-464; DOI: 10.21873/anticanres.17435

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Synthesis of Polymethoxylated 3-Styrylflavones and their Antiproliferative Activity in HL60 Cells
ARISA TSUTSUMI, SATORU KAWAII, YUKO YOSHIZAWA
Anticancer Research Feb 2025, 45 (2) 457-464; DOI: 10.21873/anticanres.17435
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Keywords

  • 3-styrylflavone
  • styryl-flavone hybrid molecule
  • Wittig reaction
  • antiproliferative activity
  • HL60 cells
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