Formylation of a metathesis-derived ansa[4]-ferrocene: a simple route to anticancer organometallics. Issue 33 (6th July 2020)

• Record Type: Journal Article
• Authors: Mazur, Maria; Mrozowicz, Michał; Buchowicz, Włodzimierz; Koszytkowska-Stawińska, Mariola; Kamiński, Radosław; Ochal, Zbigniew; Wińska, Patrycja; Bretner, Maria
• Is Part Of: Dalton transactions. Volume 49:Issue 33(2020)
• Page Start: 11504
• Page End: 11511
• Publication Date: 2020-07-06
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/d0dt01975e
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Ansa -Ferrocenealdehyde, obtained by formylation of a metathesis-derived ansa -ferrocene, was transformed into a conjugate with triazole and uracil with anticancer activity. 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 P 21 21 21 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.