A new variety of adamantyl chalcones (2, 3a-3o) were efficiently prepared by Claisen-Schmidt reaction of 4-adamantyl acetophenone 2 with a serie of aromatic aldehydes in good yields. Their structures were confirmed by spectroscopic data, and the relative configuration of 3d was confirmed by X-ray crystallography. All synthesized chalcones were tested against a panel of Grampositive and Gram-negative bacteria and pathogenic fungus and displayed strong antibacterial activity against Enterococcus faecali 29212, Pseudomonas aeruginosa ATCC27853, Escherichia coli and interesting antifungal activity against Candida glabrata ATCC 90030. The effect of these compounds was also tested in vitro as antitumor on Miapaca2 cells. Compounds also showed anticancer activity against human pancreas cancer cell MiaPaca2.
New adamantyl chalcones: Synthesis, antimicrobial and anticancer activities
CAPORALE, ANGELAMARIA;SATURNINO, Carmela;ARRA, CLAUDIO;RASTRELLI, Luca
2017-01-01
Abstract
A new variety of adamantyl chalcones (2, 3a-3o) were efficiently prepared by Claisen-Schmidt reaction of 4-adamantyl acetophenone 2 with a serie of aromatic aldehydes in good yields. Their structures were confirmed by spectroscopic data, and the relative configuration of 3d was confirmed by X-ray crystallography. All synthesized chalcones were tested against a panel of Grampositive and Gram-negative bacteria and pathogenic fungus and displayed strong antibacterial activity against Enterococcus faecali 29212, Pseudomonas aeruginosa ATCC27853, Escherichia coli and interesting antifungal activity against Candida glabrata ATCC 90030. The effect of these compounds was also tested in vitro as antitumor on Miapaca2 cells. Compounds also showed anticancer activity against human pancreas cancer cell MiaPaca2.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
