title: Antioxidant properties of Mannich bases.
abstract: 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.
authors.affiliation: Department of Biomedicinal Chemistry, Inje University, Gimhae 621-749, Gyeongnam, South Korea.
authors.forename: Dong Ho
authors.initials: DH
authors.lastname: Park
authors.forename: Jayachandran
authors.initials: J
authors.lastname: Venkatesan
authors.forename: Se-Kwon
authors.initials: SK
authors.lastname: Kim
authors.forename: Venkatachalm
authors.initials: V
authors.lastname: Ramkumar
authors.forename: Paramasivam
authors.initials: P
authors.lastname: Parthiban
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001205:Ascorbic Acid / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D002460:Cell Line; D003474:Curcumin / Q000031:analogs & derivatives* / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D008352:Mannich Bases / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010851:Picrates / Q000737:chemistry; D017382:Reactive Oxygen Species / Q000037:antagonists & inhibitors / Q000378:metabolism; D012822:Silicon Dioxide / Q000737:chemistry; D024502:alpha-Tocopherol / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D001880:Boranes; D008352:Mannich Bases; D010851:Picrates; D017382:Reactive Oxygen Species; D012822:Silicon Dioxide; C021274:boron trifluoride; C004931:1,1-diphenyl-2-picrylhydrazyl; D024502:alpha-Tocopherol; D003474:Curcumin; D001205:Ascorbic Acid