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

Abstract : 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.
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Submitted on : Friday, February 17, 2017 - 1:21:32 PM
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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, Royal Society of Chemistry, 2016, 40 (11), pp.9441--9447. ⟨10.1039/c6nj02018f⟩. ⟨hal-01414285⟩

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