Synthesis of ferrocene amides and esters from aminoferrocene and 2-substituted ferrocenecarboxylic acid and properties thereof

Palabindela Srinivas (1, 2) , Sunchu Prabhakar (2, 1) , Floris Chevallier (2) , Ekhlass Nassar (3) , William Erb (2) , Vincent Dorcet (2) , Viatcheslav Jouikov (2) , Palakodety Radha Krishna (1) , Florence Mongin (2)

1 IICT - CSIR Indian Institute of Chemical Technology
2 ISCR - Institut des Sciences Chimiques de Rennes
3 Department of Chemistry

Different ferrocenecarboxamides were synthesized from aminoferrocene and various acid coupling partners such as N-alpha-Boc-L-tryptophan and N-protected sugar amino acids ( N-Boc-3-amino-3-deoxy-1,2-O-isopropylidene-alpha-D-ribofuranoic acid, N-Boc-3-amino-3-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranoic acid and their corresponding homo- and hetero-dimers). Similarly, reactions between 2-aminoethyl ferrocenecarboxylate and N-protected sugar amino acids afforded compounds with a carboxamide functional group remotely positioned from the ferrocene core. The X-ray diffraction structure of one of them showed the presence of an intermolecular hydrogen bond between the amide functional groups. Carbonylamino ( or carbonyloxy) and oxycarbonyl 1,2-disubstituted ferrocenes were prepared either as racemic mixtures or in enantiomerically pure ( S-P) form. Their electrochemical evaluation revealed distinctive features. Interestingly, the enantiomerically pure ferrocene diester showed a large potential shift (+45 mV) in the presence of L-glutamic acid. Finally, some of the synthesized ferrocenes were evaluated for their antibacterial, antifungal and antiproliferative ( MCF-7) activities.

Mots clés: molecular recognition; crystal-structure; amino-acids; derivatives; chirality; spectroscopy; receptors; foldamers; peptides; ligands

Domaines: Chimie

Palabindela Srinivas, Sunchu Prabhakar, Floris Chevallier, Ekhlass Nassar, William Erb, et al.. Synthesis of ferrocene amides and esters from aminoferrocene and 2-substituted ferrocenecarboxylic acid and properties thereof. New Journal of Chemistry, 2016, 40 (11), pp.9441--9447. ⟨10.1039/c6nj02018f⟩. ⟨hal-01414285⟩