Canthin ‐4‐ones as Novel Antibacterial Agents

Based on the chemotype of canthin‐4‐one alkaloids with moderate antimicrobial activity, a collection of variously substituted canthin‐4‐ones and desaza analogs were synthesized. Key steps in the syntheses were regioselective halogenations of (desaza) canthin‐4‐one, followed by Pd‐catalyzed cross‐coupling reactions. The in vitro screening for antimicrobial activity revealed that two 5‐substituted canthin‐4‐ones (3‐pyridyl, 2‐bromophenyl) exhibit significant activity against Streptococcus entericus, coupled with high selectivity and the lack of cytotoxicity against mammalian cells. The intact canthin‐4‐one ring system was demonstrated to be essential for antibacterial activity. Systematic variation of the structures of canthin‐4‐one alkaloids led to novel canthin‐4‐ones with high antibacterial activity and high selectivity for Streptococcus entericus. The intact canthin‐4‐one ring system was demonstrated to be essential for antibacterial activity.
Source: Archiv der Pharmazie - Category: Drugs & Pharmacology Authors: Tags: Full Paper Source Type: research