Synthesis and crystallographic insight into the structural aspects of some novel adamantane-based ester derivatives

Kumar, C. S. C. and Kwong, H. C. and Mah, S. H. and Chia, T. S. and Loh, Wan-Sin and Quah, C. K. and Lim, G. K. and Chandraju, S. and Fun, Hoong-Kun (2015) Synthesis and crystallographic insight into the structural aspects of some novel adamantane-based ester derivatives. MOLECULES, 20 (10). pp. 18827-18846. ISSN 1420-3049

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Official URL: http://doi.org/10.3390/molecules201018827

Abstract

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 dimethylformamide medium at room temperature. Three-dimensional structures studied using X-ray diffraction suggest 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.

Item Type: Article
Uncontrolled Keywords: adamantyl; synclinal; crystal packing; antioxidant; anti-inflammatory
Subjects: D Physical Science > Sugar Technology
Divisions: PG Centre Mandya > Sugar Technology
Depositing User: Shrirekha N
Date Deposited: 30 May 2019 10:00
Last Modified: 01 Jun 2019 11:40
URI: http://eprints.uni-mysore.ac.in/id/eprint/690

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