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

Molecules

C. S. Chidan Kumar³  Huey Chong Kwong⁴  Siau Hui Mah¹  Tze Shyang Chia³  Wan-Sin Loh³  Ching Kheng Quah³  Gin Keat Lim⁴  Siddegowda Chandraju²  Hoong-Kun Fun³ 

[1] School of Biosciences, Taylor’s University, Lakeside Campus, Subang Jaya 47500, Selangor, Malaysia; E-Mail:;Department of Sugar Technology & Chemistry, University of Mysore, Sir M.V. PG Center, Mandya 571402, Karnataka, India; E-Mail:;X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia; E-Mails:;School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia; E-Mails:

关键词: adamantyl;    synclinal;    crystal packing;    antioxidant;    anti-inflammatory;   

DOI  :  10.3390/molecules201018827

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.