Synthesis and biological evaluation of aminoketones
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Date
2010
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Abstract
A three-component Mannich reaction of different ketones with aromatic aldehydes and different amines in microwave irradiation under solvent free condition afforded corresponding ?-amino carbonyl compounds in excellent yields. This method proved as a novel and improved modification of the reported three-component Mannich reaction in terms of milder reaction conditions, reaction times, clean reaction profiles, very small quantity of catalyst and simple workup procedure. Newly synthesized ?-aminoketones were characterized by spectral studies. Structure of compound 4a was also confirmed by single-crystal X-ray analysis. All the compounds were screened for their antimicrobial activity by MIC method. Few of the molecules were found to be biologically potent. © 2010 Elsevier Masson SAS. All rights reserved.
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Keywords
2 [(2 methylindol 5 ylamino)pyridin 4 yl [methyl]]cyclohexanone, 2 [(2,4 difluorophenylamino) [2 fluoromethoxyphenyl]methyl]cyclohexanone, 2 [(2,4 difluorophenylamino) [4 fluorophenyl]methyl]cyclohexanone, 2 [(3 fluorophenylamino) [2 [allyloxy]phenyl]methyl]cyclohexanone, 2 [(3 methoxyphenylamino) [2 hydroxy 3 methylphenyl]methyl]cyclohexanone, 2 [(3,4 difluorophenylamino) (2 fluorophenyl) methyl] cyclohexanone, 2 [(3,4,5 trifluorophenylamino) (4 ethylphenyl) methyl] cyclohexanone, 2 [(4 methyl 3 nitrophenylamino) [4 ethylphenyl]methyl]cyclohexanone, 2 [(4 tert butylphenylamino) [phenyl]methyl]cyclohexanone, 2 [(benzofuran 2 yl) [naphthalen 1 ylamino]methyl]cyclohexanone, 4 [(2 chlorophenyl) [2 oxocyclohexyl]methylamino]benzonitrile, aldehyde, aminoketone, antiinfective agent, beta aminoketone, unclassified drug, antimicrobial activity, article, Bacillus subtilis, catalyst, drug screening, drug structure, drug synthesis, Escherichia coli, Mannich reaction, microwave irradiation, minimum inhibitory concentration, Pseudomonas aeruginosa, Staphylococcus aureus, X ray analysis, Anti-Bacterial Agents, Crystallography, X-Ray, Ketones, Microbial Sensitivity Tests, Microwaves, Models, Molecular, Molecular Structure, Structure-Activity Relationship
Citation
European Journal of Medicinal Chemistry, 2010, 45, 12, pp. 6090-6094