Synthesis of conjugated bile acids/azastilbenes as potential antioxidant and photoprotective agents.

Abstract A series of 14 bile acids/azastilbenes conjugates ( 1a–g and 2a–g ) was prepared through the condensation of bile amides ( 1 and 2 ) and aromatic aldehydes. The newly synthesized conjugates were evaluated in vitro for their antioxidant and photoprotective activities. Six compounds ( 1 , 1a , 1b , 2 , 2a and 2b ) showed promising antioxidant activity with IC 50 values of 19.60–31.83 μg mL −1 . The synthesized compounds presented a varied photoprotection profile, with the SPF ranging from 2 to 9. Among the 16 compounds tested for the protection against UVB sunrays, 3 compounds ( 2c , 2e and 2g ) presented more significant protection than resveratrol and the free azastilbene 3 ; while the UVAPF increased from 2 in resveratrol and 5 in 3 to 5–11 in the majority of the conjugates.