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Allylic hydroxylation of cyclohexene.

Authors
Leibman-KC; Ortiz-E
Source
Fed Proc 1976 Jan; 36:666
NIOSHTIC No.
00071494
Abstract
Drugs containing cyclohexene (110838) rings (hexobarbital (56291), thiocarbanidin (92977)) are metabolically hydroxylated at the allyl position. This reaction was studied with cyclohexene (CH). Microsomes or 9000 g supernatant fractions of rats or rabbits catalyzed the conversion of CH to 2-cyclohexen-1-o1 in the presence of a reduced nicotinamide-adenine-dinucleotide-phosphate generating system; the latter could not be substituted by a reduced nicotinamide-adenine-dinucleotide generating system. Allylic hydroxylation was stimulated by magnesium ions. The product was identified by gas-liquid chromatography, direct and after formation of the trimethylsilyl-derivative, and by mass spectrometry. The reaction was induced over five-fold by phenobarbital (PB) treatment of rats. CH oxide was formed at a fraction of the rate of 2-CH-1-o1 in control preparations, but to a greater extent than the alcohol in preparations from PB treated rats. Cyclohexane-diol formation was also induced by PB. The formation of a small amount of 2-cyclohexen- 1-one could be detected in preparations from PB treated rats. SKF 525-A was a more potent inhibitor of allylic hydroxylation than was metyrapone, but both inhibitors caused greater inhibition of epoxidation than of hydroxylation. 2-CH-1-o1 or 1-one were not formed from CH oxide in-vitro. After feeding CH to rats, 2-CH-1-one was found in urine; no 2-CH-1-o1 was detected before or after hydrolysis with beta-glucuronidase.
Keywords
NIOSH-Publication; Grants-other; Hydrocarbons; Organic-solvents; Hydroxylation-reactions; Chemical-reactions; Drugs-interactions; Metabolism
Contact
Pharmacology and Therapeutics Univ of Florida Coll of Med Dept of Pharma & Therapeutics Gainesville, Fla 32601
CODEN
FEPRA7
CAS No.
110-83-8; 56-29-1; 92-97-7
Publication Date
19760101
Document Type
Abstract
Funding Amount
460733
Funding Type
Grant
Fiscal Year
1976
NTIS Accession No.
NTIS Price
Identifying No.
Grant-Number-R01-OH-00316
ISSN
0014-9446
Priority Area
Other Occupational Concerns; Grants-other
Source Name
Federation Proceedings
State
FL
Performing Organization
University of Florida Gainesville, Gainesville, Florida
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