New adamantyl chalcones: Synthesis, antimicrobial and anticancer activities

Aouatef Tabbi, Dahmane Tebbani, Angelamaria Caporale, Carmela Saturnino, Seyed Mohammad Nabavi, Palma Giuseppe, Claudio Arra, Zerrin Cantürk, Gülhan Turan-Zitouni, Hocine Merazig, Eduardo Sobarzo-Sánchez, Luca Rastrelli

Research output: Contribution to journalArticle

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.

Original languageEnglish
JournalCurrent Topics in Medicinal Chemistry
Volume17
Issue number7
DOIs
Publication statusPublished - Mar 1 2017

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Keywords

  • Activity
  • Adamantyl chalcones
  • Anticancer activity
  • Antifungal
  • Antimicrobial activity
  • MiaPaca2
  • NMR

ASJC Scopus subject areas

  • Drug Discovery

Cite this

Tabbi, A., Tebbani, D., Caporale, A., Saturnino, C., Nabavi, S. M., Giuseppe, P., Arra, C., Cantürk, Z., Turan-Zitouni, G., Merazig, H., Sobarzo-Sánchez, E., & Rastrelli, L. (2017). New adamantyl chalcones: Synthesis, antimicrobial and anticancer activities. Current Topics in Medicinal Chemistry, 17(7). https://doi.org/10.2174/1568026616666160824121935