1.
J Med Chem
; 34(8): 2356-60, 1991 Aug.
Article
in English
| MEDLINE
| ID: mdl-1875335
ABSTRACT
1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one (2) is identified as a potent antibacterial agent. A compound, 2-chloro-1-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-2-phenylpropan++ +-1-one (5) has been designed with the intention of its acting as a pro-drug, liberating the lethal species 2 specifically within the target anaerobic bacterial cell following bioreduction by bacterial ferredoxin or related electron transfer proteins. The synthesis and biological activity of 5 is described and compared with the activities of the analogous alpha-bromo ketone 6 and alpha-fluoro ketone 7. Synthesis of 6, 7, and the corresponding alpha-hydroxy ketone 11 is also described.
Subject(s)
Anti-Bacterial Agents/pharmacology , Bacteria, Anaerobic/drug effects , Imidazoles/pharmacology , Alkenes/chemistry , Alkenes/pharmacology , Anti-Bacterial Agents/chemical synthesis , Chemical Phenomena , Chemistry , Chlorobenzenes/chemistry , Chlorobenzenes/pharmacology , Chromatography, High Pressure Liquid , Imidazoles/chemical synthesis , Imidazoles/chemistry , Magnetic Resonance Spectroscopy , Metronidazole/pharmacology , Mutagenicity Tests , Prodrugs/chemical synthesis , Prodrugs/chemistry , Prodrugs/pharmacology
2.
J Chromatogr
; 225(2): 488-92, 1981 Oct 09.
Article
in English
| MEDLINE
| ID: mdl-6795218