Novel conjugates of ferrocene with uracil, 5-fluorouracil,
tegafur,
or acyclovir are reported. Their synthesis involved (i) the azide–alkyne
1,3-dipolar cycloaddition or (ii) the formation of the ester linkage.
For the first time, we present an in-depth insight into the supramolecular
interactions between β-cyclodextrin and ferrocene-nucleobase
derivatives. Spectroscopic and voltammetric analyses performed within
this work suggested that the ferrocene or adamantane unit of the conjugates
interacted with the β-cyclodextrin’s inner cavity. The
methods applied for the supramolecular studies included 1H–1H ROESY NMR, 1H NMR titration, Fourier-transform
infrared spectroscopy, cyclic voltammetry, fluorescence spectra titration,
and 1H DOSY NMR. 1H DOSY NMR was also employed
to evaluate the apparent binding constants for all the complexes.
The ferrocene–acyclovir conjugate Fc-5 featured
the highest apparent binding constant value among all the complexes
tested.
Ansa-Ferrocenealdehyde, obtained by formylation of a metathesis-derived ansa-ferrocene, was transformed into a conjugate with triazole and uracil with anticancer activity.
This paper reports the synthesis and characterization of novel monoferrocenylsumanenes obtained by means of the Sonogashira cross-coupling or click chemistry reaction as well as their application in cesium cation electrochemical sensors. A new synthetic protocol based on Sonogashira cross-coupling was developed for the synthesis of monoferrocenylsumanene or ethynylsumanene. The click chemistry reaction was introduced to the sumanene chemistry through the synthesis of 1,2,3-triazole containing monoferrocenylsumanene. The designed synthetic methods for the modification of sumanene at the aromatic position proved to be efficient and proceeded under mild conditions. The synthesized sumanene derivatives were characterized by detailed spectroscopic analyses of the synthesized sumanene derivatives. The supramolecular interactions between cesium cations and the synthesized monoferrocenylsumanenes were spectroscopically and electrochemically investigated. Furthermore, the design of the highly selective and sensitive cesium cation fluorescence and electrochemical sensors comprising the synthesized monoferrocenylsumanenes as receptor compounds was analyzed. The tested cesium cation electrochemical sensors showed excellent limit of detection values in the range of 6.0−9.0 nM. In addition, the interactions between the synthesized monoferrocenylsumanenes and cesium cations were highly selective, which was confirmed by emission spectroscopy, laser ablation inductively coupled plasma mass spectrometry (LA-ICP-MS), and cyclic voltammetry.
The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium-catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro.
Carbon-encapsulated iron nanoparticles have been functionalized with various types of organic moieties using an eco-friendly and grinding-induced cycloaddition reaction.
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