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Issue 33, 2020
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Formylation of a metathesis-derived ansa[4]-ferrocene: a simple route to anticancer organometallics

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Abstract

Formylation of ansa[4]-ferrocene, obtained through the ruthenium-catalysed olefin metathesis, yields two separable, planar chiral 1,3- and 1,2-ansa-ferrocene aldehydes. Single-crystal X-ray structure analysis reveals that both regioisomers crystallize with spontaneous resolution of the racemate in the chiral P212121 space group with one molecule in the asymmetric unit. The major 1,3-isomer was further transformed into a conjugate with 1,2,3-triazole and uracil using “click” chemistry as the key synthetic step. This inorganic–organic hybrid displays anticancer activity (MCF-7, A549, MDA-MB-231 cell lines) with EC50 values comparable to those for cisplatin.

Graphical abstract: Formylation of a metathesis-derived ansa[4]-ferrocene: a simple route to anticancer organometallics

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Article information


Submitted
02 Jun 2020
Accepted
25 Jun 2020
First published
25 Jun 2020

Dalton Trans., 2020,49, 11504-11511
Article type
Paper

Formylation of a metathesis-derived ansa[4]-ferrocene: a simple route to anticancer organometallics

M. Mazur, M. Mrozowicz, W. Buchowicz, M. Koszytkowska-Stawińska, R. Kamiński, Z. Ochal, P. Wińska and M. Bretner, Dalton Trans., 2020, 49, 11504
DOI: 10.1039/D0DT01975E

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