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Molecules 2015, 20(10), 18827-18846; doi:10.3390/molecules201018827

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

1
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
2
Department of Chemistry, Alva’s Institute of Engineering & Technology, Visvesvaraya Technological University, Mijar, Moodbidri 574225, India
3
School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia
4
School of Biosciences, Taylor’s University, Lakeside Campus, Subang Jaya 47500, Selangor, Malaysia
5
Department of Sugar Technology & Chemistry, University of Mysore, Sir M.V. PG Center, Mandya 571402, Karnataka, India
6
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 24 August 2015 / Revised: 31 August 2015 / Accepted: 5 October 2015 / Published: 16 October 2015
(This article belongs to the Section Molecular Diversity)
View Full-Text   |   Download PDF [3079 KB, uploaded 16 October 2015]   |  

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(aq), 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. View Full-Text
Keywords: adamantyl; synclinal; crystal packing; antioxidant; anti-inflammatory adamantyl; synclinal; crystal packing; antioxidant; anti-inflammatory
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Kumar, C.S.C.; Kwong, H.C.; Mah, S.H.; Chia, T.S.; Loh, W.-S.; Quah, C.K.; Lim, G.K.; Chandraju, S.; Fun, H.-K. Synthesis and Crystallographic Insight into the Structural Aspects of Some Novel Adamantane-Based Ester Derivatives. Molecules 2015, 20, 18827-18846.

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