Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives

As a result of our longstanding interest in developing naturalproduct-inspired new antibacterial agents, we recently reported the identification of abyssinone II as a promising antibacterial lead by screening a focused flavonoid and resveratrol library.43

Li Feng


Scholarcy highlights

  • Because of the emergence and spread of multidrug resistant microorganisms and pathogenic bacterial infections, novel chemotype antibacterial agents demonstrating distinct modes of action from existing antibiotics are urgently needed
  • Natural products are known as rich sources of bioactive molecules and chemical diversity and have provided invaluable chemical scaffolds as well as served as an inspiration toward antibacterial drug discovery and development.− In this context, synthesis and evaluation of natural-product-inspired compound libraries represent an attractive approach for discovering novel antibacterial agents
  • To improve the reaction efficiency and develop a modular synthesis toward olympicin A and derivatives, we evaluated diverse protecting schemes including the tertbutyldimethylsilyl, the base-stable methoxymethyl, and the p-toluenesulfonyl groups and developed an improved synthesis of 2a by using the Ts protecting strategy, improving the overall yield to 40% from 1a
  • Systematic structure−activity relationship study revealed that the phenol hydroxy groups at the 5- and 7-position of the 4-chromanone scaffold were essential for antibacterial activities
  • The flavanone derivatives bearing the lipophilic substituent on the 2-phenyl ring showed good antibacterial properties as well
  • The antibacterial agents identified from this study provide chemically modified flavonoid phytochemicals as promising antibacterial leads for further medicinal chemistry optimization in an effort to identify advanced experimental candidates with antimicrobial therapeutic potential

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