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Bioorg Med Chem Lett. 2012 Oct 15;22(20):6362-7. doi: 10.1016/j.bmcl.2012.08.080. Epub 2012 Aug 29.

Antioxidant properties of Mannich bases.

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  • 1Department of Biomedicinal Chemistry, Inje University, Gimhae 621-749, Gyeongnam, South Korea.


The biological importance of antioxidants influenced to synthesize some curcumin-related compounds as potential antioxidants. Accordingly, a series of 2,4-diaryl-3-azabicyco[3.3.1]nonan-9-ones were synthesized with polyphenolic and/or polymethoxyphenyl groups by modified Mannich condensations. The yield was significantly improved using BF(3)·SiO(2) as heterogeneous catalyst under mild conditions. Stereochemistry of all the synthesized compounds was established as twin-chair with an equatorial disposition of the aryl groups, through their NMR and XRD interpretations. The ABNs 8 (curcumin analog) and 10 (bis-demethoxycurcumin analog) showed an effective profile over curcumin, α-tocopherol, and vitamin C by chemical methods. Further, the efficiency of one of the active molecules, ABN 10, was demonstrated by its intracellular ROS inhibition activity on RAW 264.7 macrophage cells by FACS analysis in dose-dependent manner.

Copyright © 2012 Elsevier Ltd. All rights reserved.

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