Influence of Ortho Group Introduction on the Alkylation of Phenolic Hydroxyl of Apocynin
Journal Title: Journal of Pharmaceutical and Biomedical Sciences - Year 2016, Vol 6, Issue 7
Abstract
Apocynin was widely studied in inflammation and oxidative stress related diseases and showed effectiveness. Structure-activity relationship study was carried out and intended to figure out new lead compounds of better efficacy. In the structure-activity relationship study of apocynin, different ortho group introduction was found to obviously affect the alkylation of phenolic hydroxyl. In this work, different ortho substituents of apocynin phenolic hydroxyl were designed and synthesized to further discuss their influence on the reaction activity of the phenolic hydroxyl group. When compared with the introduction of electron withdrawing group, aldehyde group (–CHO), introduction of electron donating group, amine group (–NH2), at the ortho position improved the reactivity of phenolic hydroxyl. It enabled the alkylation of phenolic hydroxyl easily occurring under a mild condition with a yield increase at least 26%, thus facilitated the modification of apocynin in further steps.
Authors and Affiliations
Jiang Jie, Gao Ruitao, Ou Yang, Wang Gaofang, Li Sha
Keywords
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