Cymantrene, cyrhetrene and ferrocene nucleobase conjugates: Synthesis, structure, computational study, electrochemistry and antitrypanosomal activity

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Kowalski, Konrad, Szczupk, Lukasz, Saloman, Sebastian, Steverding, Dietmar, Jablonski, Artur, Vrcek, Valerije, Hildebrandt, Alexander, Lang, Heinrich and Rybarczyk-Pirek, Agnieszka (2017) Cymantrene, cyrhetrene and ferrocene nucleobase conjugates: Synthesis, structure, computational study, electrochemistry and antitrypanosomal activity. ChemPlusChem, 82 (2). pp. 303-314. ISSN 2192-6506

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Abstract

A series of cymantrene- and cyrhetrene-nucleobase derivatives together with the ferrocene-adenine conjugates have been prepared and characterized. The key step in synthesis of all compounds involved an N1-regioselective Michael addition of the respective nucleobase nucleophile to an in situ generated organometallic acryloyl electrophile reagent. The mechanism of this reaction was examined by DFT calculations. A single crystal X-ray diffraction study of cymantrene-adenine (5) were carried out and revealed that the plane of the adenine and the cyclopentadienyl group are almost perpendicular to each other. The cyclic voltammetry measurements on the cymantrenyl-nucleobases showed irreversible behavior for all compounds which can be explain by a ligand exchange of carbonyls with the donor functionality of the nucleobases. Cymantrene and cyrhetrene ketone nucleobases displayed significant in vitro activity against Trypanosoma brucei a causative parasite of sleeping sickness. They showed no cytotoxicity against human HL-60 cancer cells.

Item Type: Article
Uncontrolled Keywords: bioorganometalic chemistry,cymantrene,cyrhetrene,ferrocene,nucleobases,antitrypanosomal activity,sdg 3 - good health and well-being ,/dk/atira/pure/sustainabledevelopmentgoals/good_health_and_well_being
Faculty \ School: Faculty of Medicine and Health Sciences > Norwich Medical School
UEA Research Groups: Faculty of Medicine and Health Sciences > Research Groups > Gastroenterology and Gut Biology
Depositing User: Pure Connector
Date Deposited: 04 Oct 2016 16:00
Last Modified: 22 Oct 2022 01:39
URI: https://ueaeprints.uea.ac.uk/id/eprint/60745
DOI: 10.1002/cplu.201600462

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