New and efficient synthesis of CpRe(CO)3 substituted steroids

Bideau, Franck Le; Pérez‐Luna, Alejandro; Marrot, Jérôme; Rager, Marie‐Noëlle; Stéphan, Elie; Top, Siden; Jaouen, Gérard

doi:10.1016/s0040-4020(01)00263-0

Cited by 24 publications

(15 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Efforts are underway to fully characterize the products of the irreversible oxidations of both this group of cymantrene-tagged aminoquinoline compounds and the untagged ligand systems themselves. 13…”

Section: Electrochemistrymentioning

confidence: 99%

“…Although a ferrocenyl group has been the most frequently-utilized OM conjugate [6], other moieties are being increasingly investigated, especially for the purpose of employing metalcarbonyl IR absorptions as analytical markers [7,8]. Among the most promising non-ferrocenyl OM bioconjugates are the strongly IR-active Group 7 'piano-stool' moieties M(CO) 3 (η 5 -C 5 H 4 R), which have been termed cymantrene and cyrhetrene, when M = Mn and M = Re, respectively, and R = H [9][10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…Found: C, 55.35; H, 3.11; N 7.11. 1 H NMR (500 MHz, CDCl 3 ): 4.23 (s, 2H, -CH 2 -NH-Ar), 4.75 (s, 2H, Cp), 4.91 (s, 2H, Cp), 5.43 (s, 1H, -NH), 6.51-652 (m, 1H), Ar, 7.42 (d, J= 8.9Hz, 1H, Ar), 7.77 (d, J= 8.9Hz, 1H, Ar), 8.01 (s, 1H, Ar), 8.57-8.59 (m, 1H, Ar) 13. C NMR (500 MHz, CDCl 3 ): 40.6 (-CH 2 -NH-Ar), 82.1 (Cp), 83.0 (Cp) , 99.2 (Ar), 101.2 (Cp), 116.9 (Ar), 120.9 (Ar), 125.9 (Ar), 128.5 (Ar), 135.4 (Ar), 148.7 (Ar), 149.2 (Ar), 151.5 (Ar).…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and anodic electrochemistry of cymanquine and related complexes

Lam

Geiger

2016

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Three compounds have been prepared in which a 4-aminochloroquinoline moiety is covalently linked to a cyclopentadienyl manganese tricarbonyl moiety. One of these ("cymanquine", 4) is the analogue of the potent antimalarial drug ferroquine in which an FeCp group has been replaced by a Mn(CO) 3 group. The anodic electrochemistry of the new compounds was investigated in dichloromethane, using [NBu 4 ][B(C 6 F 5 ) 4 ] as the supporting electrolyte. Compared to ferroquine, oxidations of the new compounds occur at considerably more positive potentials and are highly irreversible, being located at their amine groups rather than at the organometallic center.

show abstract

Section: Electrochemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and anodic electrochemistry of cymanquine and related complexes

Lam

Geiger

2016

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

show abstract

“…5 -7 Among them, a non-radioactive CpRe(CO) 3 substituted estradiol has been shown to have an excellent binding affinity for the oestrogen receptor (ER) when the organorhenium moiety was fixed at the 17α position. 8 We have also previously described 9 Table 1). …”

Section: Introductionmentioning

confidence: 99%

Synthesis of cyclopentadienyltricarbonylrhenium substituted benzhydryl species and oestrogen receptor binding properties

Plażuk

Bideau

Pérez‐Luna

et al. 2006

Applied Organom Chemis

View full text Add to dashboard Cite

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

show abstract

“…The tin containing steroid derivatives such as triphenyltincholestroyl ether 22 have been prepared and evaluated for use as insecticide, bactericide and fungicide [33]. Steroid hormones labeled with titanium have been synthesized and evaluated for their use in assessing activity of aromatase at various pathologies.…”

mentioning

confidence: 99%