- Synthesis of 17α-(Iodovinyl)estradiol and analogous derivatives by iododestannylation of insoluble polymer-supported organotin precursors
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Iodoestrogen derivatives were prepared by iododestannylation of insoluble polymer-supported organotin precursors.
- Dumartin, Gilles,Kharboutli, Jamil,Delmond, Bernard,Frangin, Yves,Pereyre, Michel
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- Estrogenic 17α-halogen-vinylestranes
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17α-bromo-α and 17α-iodo-vinyl-estrane derivatives of general formula I STR1 wherein X is a bromine or iodine atom in Z or E position, R1 is hydrogen, hydroxy or acyloxy with up to 3 C atoms, R2 is hydrogen, alkyl with up to 3 C atom
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- Synthesis, receptor binding, and tissue distribution of (17α,20E)- and (17α,20Z)-21-[125I]Iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-d ol
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The isomeric (17α,20E)- and (17α,20Z)-(iodovinyl)estradiol derivatives 3 and 6, and their no-carrier-added (nca) [125I]iodovinyl analogues, were tested for their relative target tissue retention and binding affinity for the estrogen receptor. The (iodovinyl)estradiols 3 and 6 were prepared via destannylation of the (17α,20E)- and (17α,20Z)-tributylstannyl precursors 2 and 4 with retention of configuration. Selective formation of the E or Z isomers 2 and 4 during the reaction of 17α-ethynylestradiol 1a with tri-n-butyltin hydride was controlled by the presence or absence of the catalyst, the polarity of the solvent, and the reaction temperature. The nca [125I]iodovinyl analogues [125I]-3a and [125I]-6a were obtained in good radiochemical yield and high purity by treatment of 2a and 4a with [125I]NaI in the presence of H2O2 and chloroamine-T, respectively. Of the two isomeric iodovinyl derivatives 3 and 6, the 20Z isomer 6a exhibited the highest receptor binding affinity and the [125I]-6a gave the highest in vivo receptor-mediated target tissue uptake.
- Ali,Rousseau,Ghaffari,Van Lier
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p. 1946 - 1960
(2007/10/02)
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