Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors

Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. l-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures of l-chicoric acid 2 were synthesized for the purpose of simplifying the structure of l-chicoric acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC50 values of 10.5 and 12.0 μM, respectively, comparable to that of parent compound l-chicoric acid (IC50 = 15.7 μM).

Graphical abstractCaffeoylglycolic and caffeoylamino acid derivatives and halfmeric structures of l-chicoric acid were synthesized for HIV-1 integrase inhibitors. Compounds 2c and 3f showed comparable HIV-1 IN inhibitory activities with IC50 values of 10.5 and 12.0 μM, respectively, to parent compound l-chicoric acid (IC50 = 15.7 μM).Figure optionsDownload full-size imageDownload as PowerPoint slide