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

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 OPEN ACCESSMolecules 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.

Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies

“…In order to identify the effect of the replacement of phenyl ring with relatively more electron rich biphenyl rings on the crystal packing similarity and structure occupancy, sixteen of the present biphenyl benzoate derivatives were compared with 42 reported phenacyl benzoate derivatives and sixteen adamantyl benzoate derivatives. In contrast to the high occurrence of isostructures in adamantanyl benzoate derivatives [ 31 ], there is only a pair of isostructural crystals ( 2d and 2o ) ( Fig 3 ) is observed in the present work.…”

“…Torsion angle τ3, which interconnecting two carbonyl groups, in phenacyl benzoates tends to adopt two types of conformations, either synclinal or periplanar [ 19 ]. However, τ3 for all crystals in this report only adopts synclinal conformation, ranging from 70.26° to 89.69°, which is similar to adamantyl-based ester derivatives [ 31 ]. The torsion angle between carboxylate group and the attached phenyl ring, O1—C15—C16—C17 (τ4), is observed in the ranges from 0.04° to 16.14° and 101.32° to 178.03°.…”

Cholinesterase Inhibitory Activities of Adamantyl-Based Derivatives and Their Molecular Docking Studies

“…Inspired by the diverse bioactivities of adamantane-containing molecules, herein the AChE and BChE inhibitory activities of 18 adamantyl-based ester derivatives with varying substituents were evaluated using Ellman’s colorimetric test. As reported previously, the structure of the 18 adamantyl-based ester derivatives were confirmed by NMR, FTIR, MS and single-crystal X-ray diffraction [ 25 ]. In this study, we also investigated the in silico binding mode of the proposed ligands in AChE and BChE enzymes, in comparison with tacrine as a reference, and the molecular docking procedure was validated using tacrine as the native ligand.…”

“…General synthetic routes for 2-(adamantan-1-yl)-2-oxoethyl benzoates, 2a – q , and 2-(adamantan-1-yl)-2-oxoethyl-2-pyridinecarboxylate, 2r , are shown in Figure 5 . Synthesis methods, spectroscopy analyses, and single-crystal X-ray diffraction studies were described in detail in the previous report [ 25 ].…”

Synthesis of Six and Seven-membered Heterocyclic Molecules Containing an Adamantyl Fragment and an X-ray Crystal Structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl)methanimine

“…This development led to the synthesis and testing of hundreds of adamantylamine derivatives for different bioactivities, especially for cancer drugs. The synthesis and study of the bioactivity of (E)-N-(adamantan-1-yl)-1- (3-aryl) methanimine derivatives have been undertaken via the condensation of two components of adamantan-1ylamine together with various aromatic aldehydes in the presence of acetic acid, and some of the Department of Chemistry, College of Education for Pure Science, University Of Anbar, Al-Anbar, Iraq * Corresponding author: ahmedsatori73@gmail.com * ORCID ID: 0000-0003-4471-9191 synthesized compounds have been reported to inhibit acetylcholinesterase (ACHE) and to have anti-microbial, anti-cancer impacts in vitro and antiinflammatory (6)(7)(8)(9)(10)(11).…”