Synthesis of 17α-4-amino- and 4-iodophenylestradiols

Foy, Nicolas; Stéphan, Elie; Jaouen, Gérard

doi:10.1016/s0040-4039(00)01238-7

Cited by 13 publications

(14 citation statements)

References 12 publications

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“…The results obtained were described in a preliminary communication whose principal conclusions are summarized below. [12] Several of the classic methods for the activation of the addition of organometallics to carbonyl compounds, including use of CeCl 3 [13,14] or TiCl 4 , [15,16] were tested and found to be unsatisfactory. Activation by LiClO 4 [17] gave moderate results.…”

Section: Resultsmentioning

confidence: 99%

“…[11,12] This preliminary work opened the way for a whole series of substituted aryls attached at position 17a of estradiol. Here we present the full study extended to a biochemical study of the compounds obtained and a rationalization of their behavior by molecular modeling.…”

Section: Introductionmentioning

confidence: 97%

“…We recently improved this reaction and showed that this approach could be made viable with the aid of in situ activation with boron trifluoride etherate (BF 3 ¥ OEt 2 ) or tetramethylethylenediamine (TMEDA). [11,12] This preliminary work opened the way for a whole series of substituted aryls attached at position 17a of estradiol. Here we present the full study extended to a biochemical study of the compounds obtained and a rationalization of their behavior by molecular modeling.…”

Section: Introductionmentioning

confidence: 97%

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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: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 97%

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

et al. 2003

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“…Use of three equivalents of TMEDA per aryllithium increases the activity so much that a 60 % addition product yield of the aryllithium (R = p-C 6 H 5 -N=N-NC 5 H 8 ) was obtained with estrone benzyl ether. This addition reaction does not take place without activation [64,65].…”

Section: Modifications At C-17mentioning

confidence: 99%

Homologation of Estrone or Estradiol. Appending a Carbon Substituent Into the 3-hydroxyestra-1,3,5-triene Skeleton

Braune¹,

Deb²,

Hase³

et al. 2007

COC

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“…[50] Die Um-wandlung in die entsprechenden Amine gelingt problemlos und effizient. [53] Der Schl¸sselschritt der Synthese bestand in der Addition eines lithiierten Phenyltriazens an ÷stron. Gross, Blank und Welch f¸hrten an einer Reihe Triazen-gesch¸tzter Bromanilin-Derivate Brom-Lithium-Austauschreaktionen mit anschlie˚ender Umsetzung mit Elektrophilen durch (Schema 5).…”

Section: Verwendung Von Triazenen F¸r Schutz Und Herstellung Von Aminenunclassified

Triazene: vielseitige Verbindungen für die organische Synthese

Kimball

Haley

2002

Angew. Chem.

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Synthesis of 17α-4-amino- and 4-iodophenylestradiols

Cited by 13 publications

References 12 publications

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

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

Homologation of Estrone or Estradiol. Appending a Carbon Substituent Into the 3-hydroxyestra-1,3,5-triene Skeleton

Triazene: vielseitige Verbindungen für die organische Synthese

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