Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxy)]-1-(phenyl-2-ferrocenyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction

doi:10.1016/S0022-328X(97)00086-7

Journal of Organometallic Chemistry

Volume 541, Issues 1–2, 15 August 1997, Pages 355-361

https://doi.org/10.1016/S0022-328X(97)00086-7 Get rights and content

Abstract

As part of the search for tamoxifen substitutes that could be useful in the treatment of breast cancer, the use of organometallic complexes has been investigated. For this purpose a synthesis has been developed for ferrocifen, the prototype of this new series of complexes. Low valent titanium-mediated (TiCl₄/Zn) cross-coupling of 4-MeO-C₆H₄COPh with ferrocenyl ethyl ketone affords the corresponding but-l-ene in high yield (66%), from which ferrocifen, 3, is rapidly prepared in an overall yield of 41%.

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Citation Excerpt :
Several polyphenolic compounds containing the ferrocene moiety have been shown to be more effective anticancer agents. As a result, molecules with a ferrocenyl moiety reduce the cytotoxicity of these medications to a larger amount [9]. The capacity of ferrocene-containing compounds to connect with DNA is a viable technique for bringing ferrocene moieties close to DNA, perhaps reducing the risk of DNA damage and cell death.
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Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxy)]-1-(phenyl-2-ferrocenyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction

Abstract

Chem. Lett.

Acta Crystallogr.

Endocr. Rev.

J. Med. Chem.

J. Med. Chem.

J. Nat. Cancer Inst.

J. Med. Chem.

Breast Cancer Res. Treat.

Breast Cancer Res. Treat.

J. Steroid Biochem.

J. Chem. Soc., Chem. Commun.

Chem. Rev.

J. Organomet. Chem.

Appl. Organomet. Chem.

J. Am. Chem. Soc.

Acc. Chem. Res.