One-Pot Enantioselective Synthesis of Functionalized Pyranocoumarins and 2-Amino-4H-chromenes: Discovery of a Type of Potent Antibacterial Agent

Function-oriented design and synthesis of chiral small molecules with novel activity is a key goal in modern organic chemistry. As multiple antibiotic-resistant pathogens are emerging and causing serious diseases, the need for practical routes for the development of new types of antibacterial agents...

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Veröffentlicht in:Journal of organic chemistry 2012-01, Vol.77 (2), p.878-888
Hauptverfasser: Zhang, Gen, Zhang, Yaohu, Yan, Jiexi, Chen, Ru, Wang, Shoulei, Ma, Yunxia, Wang, Rui
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Sprache:eng
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Zusammenfassung:Function-oriented design and synthesis of chiral small molecules with novel activity is a key goal in modern organic chemistry. As multiple antibiotic-resistant pathogens are emerging and causing serious diseases, the need for practical routes for the development of new types of antibacterial agents is very urgent. Herein, we present a highly efficient process for the synthesis of optically active pyranocoumarins and 2-amino-4H-chromenes through an organocatalytic Knoevenagel/Michael/cyclization sequence, and the preliminary biological studies of these new heterocyclic compounds revealed potent antibacterial activity. This study provides a novel strategy for further research and development of new types of antibacterial agents effective against human pathogens.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo202020m