16726-19-5

A series of 9-substituted 1,2,3,4,5,6,7,8-octahydroacridine-N(10)-oxides is evaluated against 12 bacterial and fungal strains, for their microbicidal and anti-pathogenic features. The largest spectrum of the antibacterial activity is evidenced for the nitro- (2b) and hydroxy- (5b) N-oxides, followed by the amino-N-oxide (3b). Density functional theory (DFT) modeling of the molecular structure and frontier molecular orbitals, i.e. highest occupied/lowest unoccupied molecular orbital (HOMO/LUMO), is accomplished by using the GAMESS 2012 software at M11/ktzvp level of theory in order to find their structural and electronic parameters. We show that the planarity of the molecules and the presence of the electron withdrawing group are advantages for its antimicrobial activity. Finally, we briefly present and discuss results on the processing of such compounds into thin films and hybrid structures by laser-assisted techniques, i.e. matrix-assisted pulsed laser evaporation (MAPLE) or laser-induced forward transfer (LIFT), to provide simple and environmental friendly, state-of-the-art solutions for antimicrobial/medical coatings and devices.

The oxidative N-demethylation of the N-epimeric N-oxides of four stereoisomeric N-methyl-tetradecahydroacridines, with K2CrO 4, was performed with yields varying within 39-85%. The course and yield of the reaction is clearly influenced by the geometry of the tricyclic carbon framework of the parent amine, whereas the configuration of the N-methyl group (axial or equatorial) has no obvious influence upon yields.

Hydogenation of acridine (1) using a commercial Pd-Al2O3 catalyst was kinetically and stereochemically studied under variable conditions.A consecutive pathway, (1) -> 9,10-dihydroacridine (2) -> 1,2,3,4,4a,9,9a,10-octahydroacridine (5), which competes with hydrogenative isomerisation of (2) to 1,2,3,4,5,6,7,8-octahydroacridine (4) via 1,2,3,4-tetrahydroacridine (3) or (5) was suggested from the observed product distributions over the time course of the reactions and their kinetic simulation.Thus, selectivity for the hydrogenated products is found to be controlled by either kinetics or thermodymanics according to the reaction conditions.Thermodynamic stabilities of the products are discussed based on quantum chemical (MNDO) and molecular mechenics (MM2) calculations to rationalize the reaction scheme.The stereoisomers of (5) and perhydroacridine (6) were identified and quantified by detail analyses using g.c.-i.r. and (13)C n.m.r.The stereoselectivity is governed by the preference in adsorption of the intermediates on the catalyst surface at a lower reaction temperature (150 deg C); however, a higher temperature (250 deg C) produces the thermodynamically stable products through equilibrium control.

The configurations of the perhydroacridines formed in the catalytic hydroamination of threo-methylenedicyclohexanone and the product of its cyclization - 2-hydroxy-2,3-tetramethylenebicyclononan-9-one - were established by means of the 13C NMR spectra and alternative synthesis.It is shown that isomers with cis-anti-cis and cis-syn-cis configurations are formed as a result of the reactions.The results of X-ray diffraction analysis are presented for cis-syn-cis-N-(2-hydroxyethyl)perhydroacridine.

It was established that the principal pathway in the catalytic hydro(alkyl,aryl)amination of 1,5-diketones is, depending on the structure of the diketone and the amine component, the stereospecific formation of substituted piperidines, octa- and decahydroquinolines, and perhydroacridines or pyridine and tetrahydro- and benzodihydroquinoline structures.