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Paper | Regular issue | Vol 96, No. 11, 2018, pp.1910-1924
Published online, 9th November, 2018
DOI: 10.3987/COM-18-13980
Effect of meta-Substituents on the Radical Scavenging Activity of 6-Chromanol Derivatives

Keiko Inami,* Yuta Okayama, Mariko Suzuki, and Masataka Mochizuki

*Division of Pharmaceutical Organic Chemistry, Faculty of Pharmaceutical Sciences, Sanyo-Onoda City University, 1-1-1 Daigakudori, Sanyo-Onoda-shi, Yamaguchi 756-0884, Japan


A series of 8-substituted 6-chromanols, namely, the methyl- (4), methoxy- (5), amino- (6), methylamino- (7), dimethylamino- (8), 1-pyrrolidinyl- (9), piperidino- (10), 1-piperazinyl- (11), and morpholino- (12) derivatives, were synthesized and investigated to determine the effect of substitution meta to the phenolic OH group of a 6-chromanol on the radical scavenging activity. 7 and 9 possessed excellent radical scavenging properties. Our data showed that the lone-pair electrons on the nitrogen atom of the substituent at the m-position donated electron density into the conjugated p-orbitals on the 6-chromanoxyl radical by δ-donation through resonance, enhancing the radical scavenging activity.