Radioiododestannylation: preparation and evaluation of radioiodinated thienyl alcohols.
Radioiododestannylations was employed to prepare a series of four specifically labeled thienyl alcohols: 1-(5-iodo-2-thienyl)-cyclopentan-1-ol and -cyclohexan-1-ol; 17 alpha-(5-iodo-2-thienyl)-17 beta-estradiol and -estradiol-3-O-methyl ether. The method utilized 5-(trimethylstannyl)thienyl intermediates which had been prepared in good yields from 2,5-bis(trimethylstannyl)thiophene and the appropriate cyclic ketones. The trimethylstannyl substrates reacted with no-carrier-added Na125I in the presence of 30% H2O2-acetic acid (2:1) at pH 4.5 at ambient temperature for 5-15 min to give, after HPLC separation, the desired 5-[125I]iodothien-2-yl products in greater than 90% isolated yields. Although tissue distribution studies in rats were uneventful, the methodology employed to give the labeled products possesses distinct advantages compared to alternative methods for preparing radioiodinated aryl moieties.
Hanson
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Department of Medicinal Chemistry, Northeastern University, Boston, MA 02115.
Franke
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Lee
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Seitz
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D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003511:Cyclohexanols / Q000138:chemical synthesis / Q000378:metabolism; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000378:metabolism; D004958:Estradiol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000378:metabolism; D005260:Female; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D007700:Kinetics; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D013876:Thiophenes / Q000138:chemical synthesis* / Q000378:metabolism; D014018:Tissue Distribution
D003511:Cyclohexanols; D003517:Cyclopentanes; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D013876:Thiophenes; C016327:cyclopentanol; D004958:Estradiol