Schönenberger, Helmut and Bastug, T. and Bindl, L. and Adam, Adelheid and Adam, Dieter and Petter, A. and Zwez, W. (1969) Action mechanism of antimicrobial beta -amino ketones. Pharmaceutica acta Helvetiae 44 (11), pp. 691-714.
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Structure-activity relations of aliphatic beta -aminoketones, beta -aminopropiophenones, alpha -phenyl-beta -aminoketones, and alpha -phenyl-beta -aminopropiophenones against fungis, yeasts, and gram-pos., and gram-neg. bacteria showed that the fungicidal activity was due to the beta -amino ketone structure. Substitution of a Ph group on either the alpha -C or carbonyl C increased fungicidal activity, whereas substituents on either the amino group or the benzene ring had no effect. No correlations were found between the phys.-chem properties of these compds. and their resp. activity as fungicides. Addn. of Cu2+ to the beta -aminoketones did not alter their antimicrobial properties. The action of beta -aminoketones as fungicides depended on formation of active breakdown products, H2CO and alpha ,beta -unsatd. ketones; a rapid rate of breakdown indicated increased fungicidal activity. 1-Dimethylamino-2-methyl-3-phenyl-3-propanone decreased the wt. of Yoshida-sarcoma or sarcoma 180 by 40%; generally, beta -aminoketones inhibited tumor growth of sarcoma 180 in mice by 50%; aliphatic beta -aminoketones had no tumor inhibiting properties. The tumor inhibiting properties of aromatic beta -aminoketones depended on the acetylation and aminomethylation of biol. cell substituents such as enzymes, DNA, or RNA.
|Additional information (public):||CAN 72:65748 19 Pesticides 50-00-0; 73-63-2; 91-03-2; 94-38-2; 94-39-3; 98-86-2; 124-40-3; 534-84-9; 586-60-7; 768-03-6; 1892-36-0; 2138-33-2; 3506-36-3; 3670-68-6; 4380-83-0; 5782-64-9; 7353-59-5; 10122-32-4; 13315-02-1; 14459-14-4; 15451-29-3; 15687-41-9; 20451-28-9; 22104-62-7; 22563-99-1; 25527-39-3; 25527-63-3; 27702-63-2; 27702-65-4; 27702-67-6; 27702-68-7; 27876-79-5; 27876-80-8; 27876-81-9; 27876-82-0; 28118-62-9 Role: BIOL (Biological study) (biocides)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Ketones Role: BIOL (Biological study) (amino, biocidal action of, structure in relation to) Bactericides Fungicides (aminoketones) Molecular structure-biological activity relationships (biocidal, of aminoketones) amino ketone fungicides fungicides amino ketone ketone amino fungicides propiophenones fungicides|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 09:42|
|Last Modified:||19 Nov 2010 09:42|