Passerini three-component adducts as radical scavengers

被引:8
作者
Wang, Rui [1 ]
Liu, Zai-Qun [1 ]
机构
[1] Jilin Univ, Coll Chem, Dept Organ Chem, Changchun 130021, Peoples R China
关键词
Passerini-3CR; Ferrocene; Coumarin; Antioxidant; DNA oxidation; Free radical; DNA OXIDATION; SOLVENT-FREE; EFFICIENT SYNTHESIS; REACTION-PRODUCT; UGI; CHEMISTRY; ALDEHYDES; KINETICS; SYSTEM;
D O I
10.1016/j.tetlet.2015.11.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Eighteen alpha-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 alpha-acyloxycarboxamides toward DNA oxidation and radicals. In trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical and in inhibiting 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA, alpha-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. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7028 / 7033
页数:6
相关论文
共 38 条
  • [1] Stereochemical control of the Passerini reaction
    Andreana, PR
    Liu, CC
    Schreiber, SL
    [J]. ORGANIC LETTERS, 2004, 6 (23) : 4231 - 4233
  • [2] THE PASSERINI REACTION .3. STEREOCHEMISTRY AND MECHANISM
    BAKER, RH
    STANONIS, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (02) : 699 - 702
  • [3] Fast and efficient solvent-free Passerini reaction
    Bousquet, Till
    Jida, Mouhamad
    Soueidan, Mohamad
    Deprez-Poulain, Rebecca
    Agbossou-Niedercorn, Francine
    Pelinski, Lydie
    [J]. TETRAHEDRON LETTERS, 2012, 53 (03) : 306 - 308
  • [4] TOCOPHEROL-MEDIATED PEROXIDATION - THE PROOXIDANT EFFECT OF VITAMIN-E ON THE RADICAL-INITIATED OXIDATION OF HUMAN LOW-DENSITY-LIPOPROTEIN
    BOWRY, VW
    STOCKER, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6029 - 6044
  • [5] Lewis acid-catalyzed formation of Ugi four-component reaction product from Passerini three-component reaction system without an added amine
    Dai, Wei-Min
    Li, Huoming
    [J]. TETRAHEDRON, 2007, 63 (52) : 12866 - 12876
  • [6] Mechanisms of free radical-induced damage to DNA
    Dizdaroglu, Miral
    Jaruga, Pawel
    [J]. FREE RADICAL RESEARCH, 2012, 46 (04) : 382 - 419
  • [7] A novel and efficient synthesis of 3,3-disubstituted indol-2-ones via Passerini three-component reactions in the presence of 4 Å molecular sieves
    Esmaeili, Abbas Ali
    Ghalandarabad, Saeid Amini
    Jannati, Saeideh
    [J]. TETRAHEDRON LETTERS, 2013, 54 (05) : 406 - 408
  • [8] Passerini Reaction-Amine Deprotection-Acyl Migration Peptide Assembly: Efficient Formal Synthesis of Cyclotheonamide C
    Faure, Sophie
    Hjelmgaard, Thomas
    Roche, Stephane P.
    Aitken, David J.
    [J]. ORGANIC LETTERS, 2009, 11 (05) : 1167 - 1170
  • [9] Kinetics of the Oxidation of Quercetin by 2,2-Diphenyl-1-picrylhydrazyl (dpph•)
    Foti, Mario C.
    Daquino, Carmelo
    DiLabio, Gino A.
    Ingold, K. U.
    [J]. ORGANIC LETTERS, 2011, 13 (18) : 4826 - 4829
  • [10] Green Conditions for Passerini Three-Component Synthesis of Tocopherol Analogues
    Ingold, Mariana
    Lopez, Gloria V.
    Porcal, Williams
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (05): : 1093 - 1097