title: One-pot enantioselective synthesis of functionalized pyranocoumarins and 2-amino-4H-chromenes: discovery of a type of potent antibacterial agent.
abstract: 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.
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, China.
authors.forename: Gen
authors.initials: G
authors.lastname: Zhang
authors.forename: Yaohu
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jiexi
authors.initials: J
authors.lastname: Yan
authors.forename: Ru
authors.initials: R
authors.lastname: Chen
authors.forename: Shoulei
authors.initials: S
authors.lastname: Wang
authors.forename: Yunxia
authors.initials: Y
authors.lastname: Ma
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000588:Amines / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis*; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004912:Erythrocytes / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D019169:Jurkat Cells / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D039681:Pyranocoumarins / Q000138:chemical synthesis*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D036401:Toxicity Tests, Chronic
chemical_list: D000588:Amines; D000900:Anti-Bacterial Agents; D001578:Benzopyrans; D039681:Pyranocoumarins