Abstract
Eighteen α-acyloxycarboxamides were produced by Passerini three-component reaction (3CR) in order to reveal sterically synergistic effects among various functional groups on the inhibitory properties of α-acyloxycarboxamides toward DNA oxidation and radicals. In trapping 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical and in inhibiting 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA, α-acyloxycarboxamides with gallic group exhibited significant activities, which can be further enhanced by incorporation of a ferrocenyl group (derived from ferrocenylmethyl isocyanide) at another tip of the molecule. Therefore, a large volume and electron-abundant isocyanide moiety were able to increase the inhibitory effects of phenolic hydroxyl groups derived from carboxylic acid even in a conjugation-free system.
Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
