Synthesis and Biological Evaluations of N-(2-Substituted-1-carboxyl)vinylazetidinones: A Study on the Essential Structural Element for Biological Activities of ${\beta}$-Lactam Antibiotics

A series of compounds, N-(2-substituted-1-carboxy)vinylazetidinones were successfully synthesized in order to test the hypothesis that biological activities of ${\beta}$-lactam antibiotics could be attributed to the smooth flow of electrons after a nucleophilic attack at the carbonyl carbon in the ${\beta}$-lactam ring. After introduction of aminothiazolylacetamido group at 3-position of the azetidinones, their biological activities were evaluated. Their low activities led to the conclusion that the smooth electron flow in ${\beta}$-lactams in not the sufficient source for the biological activities.