- Density functional theory molecular modeling and antimicrobial behaviour of selected 1,2,3,4,5,6,7,8-octahydroacridine-N(10)-oxides
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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.
- Marinescu, Maria,Cinteza, Ludmila Otilia,Marton, George Iuliu,Marutescu, Luminita Gabriela,Chifiriuc, Mariana-Carmen,Constantinescu, Catalin
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- Hydroacridines. Part 31. Saturated amine oxides. Part 9. Study of a procedure for N-demethylation of saturated azaheterocyclic tertiary N-methylamines via their N-oxides
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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.
- Potmischil, Francisc,Dobrinescu, Claudiu,Nicolescu, Alina,Deleanu, Calin
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experimental part
p. 95 - 99
(2012/10/08)
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- The Effect of Hydrogen Sulfide on Acridine Hydrodenitrogenation on a Sulfided NiMo/Al2O3 Catalyst
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The effect of hydrogen sulfide on acridine hydrodenitrogenation over a sulfided NiMo/Al2O3 catalyst at 280-380 deg C and 10.1 MPa total pressure was studied.The result showed that the presence of H2S depressed the total C-N hydrogenolysis at a low PH2S/PH2 ratio of 1.1-79x10-5, but that it rarely affected the C-N hydrogenolysis at a ratio above 0.003.
- Nagai, Masatoshi
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p. 330 - 332
(2007/10/02)
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- Selective Hydrogenation of 9-Aminoacridine over Supported Noble Metal Catalysts
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The selective hydrogenation of 9-aminoacridine (1) into 1,2,3,4-tetrahydro-derivative (2) was searched using noble metal catalysts (Pd, Rh, Pt, and Ru) at around 80 deg C and 60 atm of H2.The Pd/Al2O3 catalyst was found most selective to produce 2 in a higher yield of 60 percent at a conversion of 97 percent.The hydrogenation pathway of 1 is discussed in comparison with that of acridine.
- Sakanishi, Kinya,Mochida, Isao,Okazaki, Hiroshi,Soeda, Mahito
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p. 319 - 322
(2007/10/02)
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- Active Sites of a Reduced Molybdena-Alumina Catalyst. A Transient Study of Hydrodenitrogenation of Carbazole and Acridine
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A response study of the hydrodenitrogenation of acridine and carbazole on a reduced MoO3/Al2O3 catalyst was performed at 300 deg C and 10.1 MPa total pressure.Acridine was strongly adsorbed on the acidic sites of the catalyst surface for hydrogenation, while carbazole was wakly adsorbed not only on the same sites as acridine, but also on the terminal oxygen anion sites in the presence in the presence of strong bases.
- Nagai, Masatoshi,Masunaga, Takashi
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p. 972 - 975
(2007/10/02)
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- Kinetics and Stereochemistry in the Catalytic Hydrogenation of Acridine
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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.
- Sakanishi, Kinya,Ohira, Masato,Mochida, Isao,Okazaki, Hiroshi,Soeda, Mahito
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p. 1769 - 1774
(2007/10/02)
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- SATURATED NITROGEN-CONTAINING HETEROCYCLES. 13. PERHYDROACRIDINES. SYNTHESIS AND STEREOCHEMISTRY
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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.
- Kriven'ko, A. P.,Nikolaeva, T. G.,Yudovich, L. M.,Komyagin, N. T.,Yanovskii, A. I.,et al.
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p. 1324 - 1329
(2007/10/02)
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- EFFICIENCY OF TWO-STAGE HYDRODENITROGENATION OF AROMATIC NITROGEN COMPOUNDS
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A high hydrodenitrogenation (86 percent) of acridine on a Ni-Mo/Al2O3 catalyst was achieved by succesive reactions at 370 deg C for 2 h and 420 deg C for 3 h, respectively, while the single stage reaction at 420 deg C for 5 h removed only 67 percent nitrogen.The effective hydrodenitrogenation is postulated due to the extensive hydrogenation in the first stage and C-N bond fission in the second stage.
- Mochida, Isao,Sakanishi, Kinya,Korai, Yozo,Fujitsu, Hiroshi
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p. 909 - 912
(2007/10/02)
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- FORMATION OF NITROGEN HETEROCYCLES IN THE HYDROAMINATION OF 1,5-DIKETONES
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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.
- Kharchenko, V. G.,Kriven'ko, A. P.,Fedotova, O. V.,Nikolaeva, T. G.
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p. 720 - 723
(2007/10/02)
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