Synthesis and antibacterial activity of four natural chalcones and their derivatives

• Published in: Tetrahedron letters Vol. 60; no. 43; pp. 151165 - 151167
• Main Authors: Li, Yuanyuan, Sun, Bingxia, Zhai, Jiadai, Fu, Lin, Zhang, Shuxin, Zhang, Jing, Liu, Hongliang, Xie, Wenhai, Deng, Hongkuan, Chen, Zhiwei, Sang, Feng
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 24.10.2019; Elsevier
• Subjects: Antibacterial activity; Chalcone; Chemistry; Chemistry, Organic; Hydroxyisoprenyl group; Natural product; Physical Sciences; Science & Technology; Natural product; Antibacterial activity; Hydroxyisoprenyl group; Chalcone; POTENT; BIOLOGICAL EVALUATION; DORSTENIA-ANGUSTICORNIS; FLAVONOIDS; TWIGS; CONSTITUENTS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2019.151165

[Display omitted] •First total syntheses of three natural chalcones were achieved.•The synthesized compounds were investigated for their antibacterial activities.•The 3′-hydroxyisoprenyl group is shown to correlate with antibacterial activities. Four natural chalcones bearing hydroxyisoprenyl or prenyl groups, named Paratocarpin E (2), Xanthoangelol D (3), Angusticornin A (4) and Kanzonol C (5), were prepared by employing the Claisen-Schmidt condensation as the key step. In an attempt to investigate the effect of the hydroxyisoprenyl group on biological activity, two of their derivatives were also prepared for antibacterial activity research. The synthesized compounds were investigated for their expected antibacterial activities against Gram positive bacteria (Bacillus subtilis, Staphylococcus aureus) as well as Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa). Paratocarpin E (2) was found to be the most potent against two Gram positive bacteria while the majority of the remaining compounds showed promising activity as well. However, all of the compounds were inactive against both Gram-negative bacteria.