In vitro oxygenation of N,N'-diphenylguanidines.
1. The enzymic C-oxygenation of N,N'-diphenylguanidine (DPG) to N-(4-hydroxyphenyl)-N'-phenylguanidine (4HPG) and the N-oxygenation of N,N'-bis-(pentafluorophenyl)-guanidine (BPG) to N"-hydroxy-N,N"-bis-(pentafluorophenyl)-guanidine (HBPG) is reported. 2. The metabolites were identified by t.l.c. and mass spectral analysis using synthetic reference compounds. 3. Rat and rabbit liver homogenates (9000 g supernatant and microsomes) were used as enzyme source. 4. The enzymic oxygenations were both O2 and NADPH dependent. NADPH could not be replaced by hydrogen peroxide. 5. 15N-n.m.r. spectroscopy was used to elucidate structure and tautomerism of BPG and HBPG.
Clement
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B
Pharmazeutisches Institut, Christian-Albrechts-Universität Kiel, Germany.
Kunze
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T
D000818:Animals; D001711:Biotransformation; D006146:Guanidines / Q000378:metabolism* / Q000493:pharmacokinetics; D066298:In Vitro Techniques; D008862:Microsomes, Liver / Q000201:enzymology; D010084:Oxidation-Reduction; D010636:Phenols / Q000378:metabolism; D011817:Rabbits; D051381:Rats
D006146:Guanidines; D010636:Phenols; C027773:diphenylguanidine