New myocardial imaging agents: synthesis of 15-(p-iodophenyl)-3(R,S)-methylpentadecanoic acid by decomposition of a 3,3-(1. 5-Pentanediyl)triazene precursor
Methods have been developed for the rapid, regiospecific introduction of iodine into the para position of the terminal phenyl ring of 15-(p-iodophenyl)-3(R,S)-methylpentadecanoic acid via the HI decomposition of a 3,3-(1,5-pentanediyl)triazene derivative of the p-amino substrate. The syntheses and physical properties of the triazene intermediate, 1-(4-(13(R,S)-methyl-14-carboxytetradecyl)phenyl)-3,3-(1,5-pentanediyl)triazene, and 15-(p-iodophenyl)-3(R,S)-methylpentadecanoic acid are described. Radioiodinated methyl-branched long-chain fatty acids such as 15-(p-iodophenyl)-3(R,S)-methylpentadecanoic acid are of interest as myocardial imaging agents as a result of the pronounced uptake and prolonged heart retention, which appears to result from the inhibition of fatty acid metabolism. Iodine was introduced into the para position of the terminal phenyl ring by treatment of the triazene intermediate at 0-5/sup 0/C with HI which was generated by in situ treatment of sodium iodide in acetone with trifluoroacetic acid. The triazene intermediate decomposed to yield exclusively the p-iodophenyl product in good yield (> 50%). These results suggest that the decomposition of the 3,3-(1,5-pentanediyl)triazene derivative of terminal phenyl long-chain fatty acids is an attractive method for the preparation of high specific activity regiospecific radioiodinated agents. 22 references.
- Research Organization:
- Oak Ridge National Lab., TN
- DOE Contract Number:
- AC05-84OR21400
- OSTI ID:
- 6614049
- Journal Information:
- J. Org. Chem.; (United States), Vol. 49:13
- Country of Publication:
- United States
- Language:
- English
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DECANOIC ACID
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
ORGANIC IODINE COMPOUNDS
TRIAZINES
DECOMPOSITION
IODINATION
ACETONE
ALKANES
AROMATICS
EXPERIMENTAL DATA
HYDRIODIC ACID
IODINATED AROMATIC HYDROCARBONS
LABELLED COMPOUNDS
NMR SPECTRA
ORGANIC FLUORINE COMPOUNDS
RADIOPHARMACEUTICALS
SODIUM IODIDES
ALKALI METAL COMPOUNDS
AZINES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DATA
DRUGS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN COMPOUNDS
INFORMATION
INORGANIC ACIDS
INORGANIC PHOSPHORS
IODIDES
IODINE COMPOUNDS
KETONES
MONOCARBOXYLIC ACIDS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHOSPHORS
SODIUM COMPOUNDS
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400702* - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials