Soft Cleavage of THP Protected Estradiols Mediated by TMSI

Foy, Nicolas; Stéphan, Elie; Jaouen, Gérard

doi:10.3184/030823401103168938

Cited by 5 publications

(1 citation statement)

References 6 publications

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“…The desired deprotection does indeed occur and is quantitative. This recently described method [22] is interesting, since it avoids the dehydration of the tertiary benzyl alcohol that we consistently observed with standard methods. We suppose that the alcohol group at position 17b was silylated in situ, which certainly obviates dehydration.…”

Section: Deprotectionsmentioning

confidence: 89%

Synthesis, Receptor Binding, Molecular Modeling, and Proliferative Assays of a Series of 17α‐Arylestradiols

et al. 2003

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A series of new derivatives of estradiol substituted at position 17alpha by various aryls has been synthesized. This was made possible by efficient activation methods for the addition of aryllithiums to the carbonyl group at position 17 of estrone by using tetramethylethylenediamine (TMEDA) or BF3 x OEt2. Their relative binding affinity (RBA) for the alpha and the beta forms of the estrogen receptor (ER) have been measured. All except one of the compounds synthesized had an RBA value of around 10 % which indicates a level of tolerance towards the bulky substituent at position 17. The lipophilicity values measured for these compounds are higher than that found for estradiol (E2). A study of their proliferative/antiproliferative effects was carried out on hormone-dependent (MCF7) and hormone-independent (MDA-MB231) breast cancer cell lines. It is interesting to note that all the compounds are estrogenic. The possibility of easily attaching an iodine at the end of a phenyl spacer opens up a route to new radiopharmaceuticals for use in radioimaging.

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Section: Deprotectionsmentioning

confidence: 89%