Cymantrene, Cyrhetrene and Ferrocene Nucleobase Conjugates: Synthesis, Structure, Computational Study, Electrochemistry and Antitrypanosomal Activity

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

[img]
Preview
PDF (Accepted manuscript) - Submitted Version
Download (1MB) | Preview

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
Faculty \ School: Faculty of Medicine and Health Sciences > Norwich Medical School
Depositing User: Pure Connector
Date Deposited: 04 Oct 2016 16:00
Last Modified: 21 Sep 2020 23:47
URI: https://ueaeprints.uea.ac.uk/id/eprint/60745
DOI: 10.1002/cplu.201600462

Actions (login required)

View Item View Item