Chemical and biochemical transformations of 5-ethoxycarbonyl-5-phenyl-2-isoxazolines.
The salts, 2-methyl-5,5-disubstituted 4,5-dihydroisoxazolium methylsulfates comprising various substituents at the C-3 carbon atom were subjected to transformations. The structure of applied compounds permitted to monitor the effect of this factor on the transformation course of the 2-isoxazoline ring. The nucleophilic addition of cyanide anion to the selected salts enabled the obtaining of a next heterocyclic system of changed physicochemical and biological properties in comparison to the starting 2-isoxazolines. The diastereoselective hydrolysis of the cyanide group in 2-isoxazolidines by the bacteria strain Rhodococcus rhodochrous PCM 909 leads to the obtaining of a racemic mixture of the trans-hydroxyacid. The introduction of new functional groups into the heterocyclic ring made these compounds attractive objects for further chemical and microbial transformations and to study their biological activity.
Zadrozna
Irmina
I
Faculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warsaw, Poland. zadrozna@ch.pw.edu.pl
Kurkowska
Joanna
J
Kruszewska
Hanna
H
D000890:Anti-Infective Agents / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D002934:Cinnamates / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D007555:Isoxazoles / Q000737:chemistry / Q000378:metabolism*; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction; D012240:Rhodococcus / Q000378:metabolism*; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D002934:Cinnamates; D003486:Cyanides; D006571:Heterocyclic Compounds; D007555:Isoxazoles; D009570:Nitriles; C029010:cinnamic acid