engleski

PREPARATION OF FERROCENOYL-NUCLEOBASE CONJUGATES BY ONE-STEP SYNTHETIC ROUTE

Nucleosides are a large family of natural compounds and their chemically modified analogs, which are characterized by great structural diversity. The sugar unit in these molecules is frequently modified (e.g. in AZT or gemcitabine) or completely replaced (e.g. in abacovir and acyclovir) [1]. Due to its stability, ease of functionalisation and potential for novel modes of action through its redox properties, ferrocene has been in the centre of bioorganometallic medicinal chemistry field [2]. Preparation of ferrocene nucleobase derivatives is based on synthetic copulation of the organometallic moiety and the heterocyclic base using the carbonyl group as the bridge [3]. Our focus in this research is on preparation of a series of novel ferrocene-modified nucleobases from nucleobases and ferrocenoyl chloride by one-step method. The ferrocenoyl units have been successfully introduced into different N- positions of the purine (type I and II) and pyrimidine (type III) ring systems (Figure 1). The position of substitution in products and the reaction regioselectivity will be explored by spectroscopy methods (1D and 2D-NMR, FTIR) and quantum chemical calculations (DFT level of theory).

ferrocenoyl-nucleobase conjugate, regioselectivity, biological activity

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