Synthesis, anti-HIV and anti-oxidant activities of caffeoyl 5,6-anhydroquinic acid derivatives

Abstract In our continued research on chlorogenic acid analogues and derivatives with improved bioactivity, we have synthesized some caffeoyl 5,6-anhydroquinic acid derivatives. The 1,7 acetonides of chlorogenic acid ( 15 ), and of the mono-caffeoyl 5,6-anhydroquinic acids ( 7 – 8 ) showed appreciable anti-HIV activity. The 3,4-dicaffeoyl 5,6-anhydroquinic acid ( 12 ) exhibited an anti-HIV activity twice as that of 3,5-dicaffeoylquinic acid ( 22 ). The caffeoyl 5,6-anhydroquinic acid derivatives displayed potent anti-oxidant activities. The mono-caffeoyl 5,6-anhydroquinic acids ( 10–11 ) were more than twice stronger than chlorogenic acid ( 21 ) on SOD-like activity.