Synthesis and Crystallographic Insight into the Structural Aspects of Some Novel Adamantane-Based Ester Derivatives

C. Kumar, Huey Kwong, Siau Mah, Tze Chia, Wan-Sin Loh, Ching Quah, Gin Lim, Siddegowda Chandraju, Hoong-Kun Fun
2015 Molecules  
Adamantyl-based compounds are commercially important in the treatments for neurological conditions and type-2 diabetes, aside from their anti-viral abilities. Their values in drug design are chronicled as multi-dimensional. In the present study, a series of 2-(adamantan-1-yl)-2-oxoethyl benzoates, 2(a-q), and 2-(adamantan-1-yl)-2-oxoethyl 2-pyridinecarboxylate, 2r, were synthesized by reacting 1-adamantyl bromomethyl ketone with various carboxylic acids using potassium carbonate in
more » ... ate in dimethylformamide medium at room temperature. Three-dimensional structures studied using X-ray diffraction suggest OPEN ACCESS Molecules 2015, 20 18828 that the adamantyl moiety can serve as an efficient building block to synthesize 2-oxopropyl benzoate derivatives with synclinal conformation with a looser-packed crystal packing system . Compounds 2a, 2b, 2f, 2g, 2i, 2j, 2m, 2n, 2o, 2q and 2r exhibit strong antioxidant activities in the hydrogen peroxide radical scavenging test. Furthermore, three compounds, 2p, 2q and 2r, show good anti-inflammatory activities in the evaluation of albumin denaturation.
doi:10.3390/molecules201018827 pmid:26501248 fatcat:w3elknsjb5gprojrhid5zuwpce