Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation
Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.
An, Taeyang,Lee, Yan
supporting information
p. 9163 - 9167
(2021/11/24)
Ligustrazine derivatives. Part 6: Design, synthesis and evaluation of novel ligustrazinyl acylguanidine derivatives as potential cardiovascular agents
A series of novel Ligustrazinyl acylguanidines was designed, synthesized and evaluated for their protective effect on injured vascular endothelial cell (ECV-304). The preliminary results demonstrated that some compounds possessed more potent activities than that of Ligustrazine in stimulating replication of the injured endothelial cell. Among the active compounds, compounds 8b, 8f and 8l displayed remarkable antioxidative activity with low EC50 values of 0.097, 0.059 and 0.094 mM, respectively. Structure-activity relationships were briefly discussed.