Synthesis of cyclopentadienyltricarbonylrhenium substituted benzhydryl species and oestrogen receptor binding properties

作者: D. Plażuk , F. Le Bideau , A. Pérez-Luna , E. Stéphan , A. Vessières

DOI: 10.1002/AOC.1034

关键词: TransmetalationReaction conditionsBinding propertiesMethyllithiumFulveneNucleophileChemistryStereochemistryOestrogen receptor

摘要: 6-(4-Methoxyphenyl)fulvene has been efficiently engaged in a process implying nucleophilic attack of methyllithium followed by transmetallation reaction the presence different organorhenium sources {XRe(CO)5: X = Cl, Br, OTf; BrRe(CH3CN)2(CO)3, [BrRe(CO)3THF]2} to afford corresponding cyclopentadienyltricarbonylrhenium-substituted compound. This study allowed us determine best complex for that transformation, and similar conditions were used with success provide new potential radiopharmaceuticals cold series. One these compounds [the (4,4′-dihydroxybenzhydryl)cyclopentadienyltricarbonylrhenium] displays good recognition α form oestrogen receptor. Copyright © 2006 John Wiley & Sons, Ltd.

参考文章(27)
Domenico Osella, Francesco Galeotti, Giorgio Cavigiolio, Carlo Nervi, Kenneth I. Hardcastle, Anne Vessières, Gerard Jaouen, The Hexacarbonyl(ethyne)dicobalt Unit: An Androgen Tag Helvetica Chimica Acta. ,vol. 85, pp. 2918- 2925 ,(2002) , 10.1002/1522-2675(200209)85:9<2918::AID-HLCA2918>3.0.CO;2-W
Siden Top, Hassane El Hafa, Anne Vessieres, Jacques Quivy, Jacqueline Vaissermann, Donald W. Hughes, Michael J. McGlinchey, Jean-Paul Mornon, Etienne Thoreau, Gerard Jaouen, Rhenium Carbonyl Complexes of .beta.-Estradiol Derivatives with High Affinity for the Estradiol Receptor: An Approach to Selective Organometallic Radiopharmaceuticals Journal of the American Chemical Society. ,vol. 117, pp. 8372- 8380 ,(1995) , 10.1021/JA00137A010
Eric S Mull, Viswajanani J Sattigeri, Alice L Rodriguez, John A Katzenellenbogen, Aryl cyclopentadienyl tricarbonyl rhenium complexes: novel ligands for the estrogen receptor with potential use as estrogen radiopharmaceuticals. Bioorganic & Medicinal Chemistry. ,vol. 10, pp. 1381- 1398 ,(2002) , 10.1016/S0968-0896(01)00406-0
Jason B. Matthews, Ken Twomey, Timothy R. Zacharewski, In Vitro and in Vivo Interactions of Bisphenol A and Its Metabolite, Bisphenol A Glucuronide, with Estrogen Receptors α and β Chemical Research in Toxicology. ,vol. 14, pp. 149- 157 ,(2001) , 10.1021/TX0001833
Stéphane Masi, Siden Top, Leila Boubekeur, Gérard Jaouen, Stefan Mundwiler, Bernhard Spingler, Roger Alberto, Direct Synthesis of Tricarbonyl(cyclopentadienyl)rhenium and Tricarbonyl(cyclopentadienyl)technetium Units from Ferrocenyl Moieties − Preparation of 17α‐Ethynylestradiol Derivatives Bearing a Tricarbonyl(cyclopentadienyl)technetium Group European Journal of Inorganic Chemistry. ,vol. 2004, pp. 2013- 2017 ,(2004) , 10.1002/EJIC.200300731
Martin G. Pomper, Henry VanBrocklin, Andrea M. Thieme, Ralph D. Thomas, Dale O. Kiesewetter, Kathryn E. Carlson, Carla J. Mathias, Michael J. Welch, John A. Katzenellenbogen, 11 beta-methoxy-, 11 beta-ethyl- and 17 alpha-ethynyl-substituted 16 alpha-fluoroestradiols: receptor-based imaging agents with enhanced uptake efficiency and selectivity. Journal of Medicinal Chemistry. ,vol. 33, pp. 3143- 3155 ,(1990) , 10.1021/JM00174A009
Sung-Hoon Kim, John A. Katzenellenbogen, Triarylethylene bisphenols with a novel cycle are ligands for the estrogen receptor. Bioorganic & Medicinal Chemistry. ,vol. 8, pp. 785- 793 ,(2000) , 10.1016/S0968-0896(00)00016-X
Franck Le Bideau, Michèle Salmain, Siden Top, Gérard Jaouen, New and efficient routes to biomolecules substituted with cyclopentadienyltricarbonylrhenium and -technetium derivatives. Chemistry: A European Journal. ,vol. 7, pp. 2289- 2294 ,(2001) , 10.1002/1521-3765(20010601)7:11<2289::AID-CHEM22890>3.0.CO;2-R