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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
2
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pubmed:dateCreated |
1995-7-6
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pubmed:abstractText |
The monofunctionalized dihydrodiol metabolites of 7,9-dimethylbenz[c]acridine and 7,10-dimethylbenz[c]acridine formed in incubations with rat liver microsomes from untreated and phenobarbital and 3-methylcholanthrene-pretreated rats were isolated by reversed-phase high performance liquid chromatography. The relative amounts of each enantiomer were determined by HPLC of diastereoisomeric esters with (+)-(1R,2S,4S)-endo-1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]hept-5 e ne-2- carboxylic acid (HCA). For the K-region dihydrodiols, absolute configurations were determined from their circular dichroic spectra using the empirical method. The absolute configuration of 3,4-dihydrodiol of 7,9-dimethylbenz[c]acridine was determined by the exciton chirality method from the CD spectrum of its bis-4-(dimethylamino)benzoate ester. For the 8,9-dihydrodiol of 7,10-dimethylbenz[c]acridine the absolute configurations were tentatively assigned by normal-phase HPLC comparison of the (+)-HCA esters with literature data. In every case the R,R-configuration predominated with optical purities > 86% for non-K-region dihydrodiols and 56-68% for the K-region dihydrodiols.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
0893-228X
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
8
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
203-8
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:7766802-Acridines,
pubmed-meshheading:7766802-Animals,
pubmed-meshheading:7766802-Carcinogens,
pubmed-meshheading:7766802-Circular Dichroism,
pubmed-meshheading:7766802-Magnetic Resonance Spectroscopy,
pubmed-meshheading:7766802-Male,
pubmed-meshheading:7766802-Microsomes, Liver,
pubmed-meshheading:7766802-Molecular Conformation,
pubmed-meshheading:7766802-Rats,
pubmed-meshheading:7766802-Rats, Sprague-Dawley,
pubmed-meshheading:7766802-Spectrophotometry, Ultraviolet
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pubmed:year |
1995
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pubmed:articleTitle |
The stereochemistry of the major rat hepatic microsomal metabolites of 7,9-dimethylbenz[c]acridine and 7,10-dimethylbenz[c]acridine.
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pubmed:affiliation |
Department of Pharmacy, University of Sydney, NSW, Australia.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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