title: Ugi multicomponent reaction product: the inhibitive effect on DNA oxidation depends upon the isocyanide moiety.
abstract: The hydroxyl-substituted benzoic acid (as phenyl group A in the product), aniline (as phenyl group B in the product), benzaldehyde (as phenyl group C in the product), and four isocyanides are employed to synthesize bis-amide via an Ugi four-component reaction. The effects of the obtained 20 bis-amides on quenching radicals and inhibiting DNA oxidation are estimated. It is found that the antioxidant effectiveness of bis-amide generated by hydroxyl groups is markedly influenced by the structural feature derived from isocyanide. The phenolic hydroxyl group attaching to phenyl group A plays a major role in scavenging radicals, and the radical-scavenging property is reinforced by the structural moiety introduced from ferrocenylmethyl isocyanide. The same conclusion is also obtained when bis-amides are used to inhibit DNA oxidation. It is still found that the ferrocenylmethyl moiety enhances the antioxidant effect of hydroxyl group at phenyl group A in protecting DNA against the oxidation. Moreover, when the bis-amide is prepared by the same isocyanide, e.g. ethyl isocyanoacetate, it is found that the hydroxyl group at phenyl group C plays the major role in inhibiting DNA oxidation, followed by the hydroxyl groups attaching to phenyl groups B and A.
authors: Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, People's Republic of China.
authors: Rui
authors: R
authors: Wang
authors: Zai-Qun
authors: ZQ
authors: Liu
mesh_terms: D000577:Amides / Q000737:chemistry / Q000494:pharmacology*; D000578:Amidines / Q000494:pharmacology; D000814:Aniline Compounds / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D004247:DNA / Q000037:antagonists & inhibitors* / Q000737:chemistry; D004249:DNA Damage / Q000187:drug effects; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000577:Amides; D000578:Amidines; D000814:Aniline Compounds; D001547:Benzaldehydes; D003486:Cyanides; C046728:2,2'-azobis(2-amidinopropane); D019817:Benzoic Acid; D004247:DNA; C023650:aniline; C032175:benzaldehyde