| pubmed-article:6292424 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C0040300 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C0014939 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C0030866 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C0243144 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C1515655 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C1521840 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C0617403 | lld:lifeskim |
| pubmed-article:6292424 | lifeskim:mentions | umls-concept:C0617405 | lld:lifeskim |
| pubmed-article:6292424 | pubmed:issue | 11 | lld:pubmed |
| pubmed-article:6292424 | pubmed:dateCreated | 1983-1-19 | lld:pubmed |
| pubmed-article:6292424 | pubmed:abstractText | Two gamma-emitting estrogen analogues, (2R*,3S*)-1-[125I]iodo-2,3-bis(4-hydroxyphenyl)pentane ([125I]iodonorhexestrol) and (2R*,3S*)-1-[77Br]bromo-2,3-bis(4-hydroxyphenyl]pentane ([77Br]bromonorhexestrol), have been prepared by halide ion displacement on a labile trifluoromethanesulfonate derivative of a suitably protected precursor, followed by mild acid deprotection. Although halide displacement on a more stable tristrifluoromethanesulfonate derivative was successful, the basic conditions required for deprotection of this precursor resulted in destruction of the products by a base-induced spiroelimination reaction. In immature female rats, both of these halonorhexestrols demonstrated preferential uptake by the uterus that could be blocked selectively by coadministration of a large dose of unlabeled estradiol. In a double label comparison with 16 alpha-[125I]iodo-17 beta-estradiol the uterine uptake of [77Br]bromonorhexestrol was notably less selective. Stability studies in vitro and in vitro have indicated that both iodo- and bromonorhexestrol are quite labile, and this lability compromises the selectivity of their uptake by estrogen target tissues in vivo. p-Hydroxyphenethyl halides are known to be unusually prone to a base-catalyzed solvolysis, via cyclization of the phenolate to a spirocyclohexadienone intermediate. This unusual solvolytic mechanism may contribute to the lability of these halonorhexestrols in vivo. | lld:pubmed |
| pubmed-article:6292424 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:language | eng | lld:pubmed |
| pubmed-article:6292424 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:6292424 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:6292424 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:6292424 | pubmed:month | Nov | lld:pubmed |
| pubmed-article:6292424 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:6292424 | pubmed:author | pubmed-author:WelchM JMJ | lld:pubmed |
| pubmed-article:6292424 | pubmed:author | pubmed-author:Katzenellenbo... | lld:pubmed |
| pubmed-article:6292424 | pubmed:author | pubmed-author:McElvanyK DKD | lld:pubmed |
| pubmed-article:6292424 | pubmed:author | pubmed-author:LandvatterS... | lld:pubmed |
| pubmed-article:6292424 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:6292424 | pubmed:volume | 25 | lld:pubmed |
| pubmed-article:6292424 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:6292424 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:6292424 | pubmed:pagination | 1307-12 | lld:pubmed |
| pubmed-article:6292424 | pubmed:dateRevised | 2007-11-14 | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:meshHeading | pubmed-meshheading:6292424-... | lld:pubmed |
| pubmed-article:6292424 | pubmed:year | 1982 | lld:pubmed |
| pubmed-article:6292424 | pubmed:articleTitle | (2R*,3S*)-1-[125I]Iodo-2,3-bis(4-hydroxyphenyl)pentane ([125I]iodonorhexestrol) and (2R*,3S*)-1-[77Br]Bromo-2,3-bis(4-hydroxyphenyl)pentane ([77Br]bromonorhexestrol), two gamma-emitting estrogens that show receptor-mediated uptake by target tissues in vivo. | lld:pubmed |
| pubmed-article:6292424 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:6292424 | pubmed:publicationType | In Vitro | lld:pubmed |
| pubmed-article:6292424 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
| pubmed-article:6292424 | pubmed:publicationType | Research Support, U.S. Gov't, Non-P.H.S. | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:6292424 | lld:chembl |
| http://linkedlifedata.com/r... | pubmed:referesTo | pubmed-article:6292424 | lld:pubmed |
| http://linkedlifedata.com/r... | pubmed:referesTo | pubmed-article:6292424 | lld:pubmed |
