دورية أكاديمية
(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.
| العنوان: | (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. |
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| المؤلفون: | Landvatter SW, Katzenellenbogen JA, McElvany KD, Welch MJ |
| المصدر: | Journal of medicinal chemistry [J Med Chem] 1982 Nov; Vol. 25 (11), pp. 1307-12. |
| نوع المنشور: | Journal Article; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S. |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 9716531 Publication Model: Print Cited Medium: Print ISSN: 0022-2623 (Print) Linking ISSN: 00222623 NLM ISO Abbreviation: J Med Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Washington Dc : American Chemical Society Original Publication: [Easton, Pa.] : American Chemical Society, [c1963- |
| مواضيع طبية MeSH: | Estradiol Congeners/*chemical synthesis , Hexestrol/*analogs & derivatives , Receptors, Estrogen/*metabolism, Animals ; Bromine ; Drug Stability ; Estradiol Congeners/metabolism ; Female ; Hexestrol/chemical synthesis ; Hexestrol/pharmacology ; In Vitro Techniques ; Iodine Radioisotopes ; Isotope Labeling ; Radioisotopes ; Rats ; Time Factors ; Tissue Distribution |
| مستخلص: | 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. |
| معلومات مُعتمدة: | R01, CA 25836 United States CA NCI NIH HHS |
| المشرفين على المادة: | 0 (Estradiol Congeners) 0 (Iodine Radioisotopes) 0 (Radioisotopes) 0 (Receptors, Estrogen) 10BI795R7D (Hexestrol) 83181-42-4 (iodonorhexestrol) 83181-43-5 (bromonorhexestrol) SBV4XY874G (Bromine) |
| تواريخ الأحداث: | Date Created: 19821101 Date Completed: 19830119 Latest Revision: 20190709 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1021/jm00353a007 |
| PMID: | 6292424 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 0022-2623 |
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| DOI: | 10.1021/jm00353a007 |