Naslov
Ferrocenoylation of uracil and its derivatives

Autori
Lapić, Jasmina ; Toma, Mateja ; Šakić, Davor ; Vrček, Valerije ; Djaković, Senka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
26. Hrvatski skup kemičara i kemijskih inženjera / Galić, Nives ; Rogošić, Marko - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2019, 97-97

ISBN
978-953-6894-67-3

Skup
26. hrvatski skup kemičara i kemijskih inženjera (26HSKIKI) ; 4. simpozij Vladimir Prelog

Mjesto i datum
Šibenik, Hrvatska, 09.04.2019. - 12.04.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
modified nucleosides ; ferrocene‐labeled pyrimidine derivatives ; regioselectivity ; spectroscopic study ; DFT calculation

Sažetak
Modified nucleosides and their components have been in the focus of chemical studies for decades, since the structural modification of nucleosides significantly alters their chemical properties and, therefore, their biological activities. As a result, many modified nucleosides have found therapeutic applications, mainly as antiviral and anticancer drugs [1]. The interest in ferrocenyl derivatives was motivated by the unique properties displayed by ferrocene, in particular its redox features, membrane permeability and low toxicity. The rationale for the introduction of the ferrocenyl group into the nucleoside skeleton is well justified by the expectation for obtaining new classes of genetic information carriers enforced by additional redox‐active properties [2]. In search for bioorganometallic systems with an extended conjugation, our research group has prepared ferrocenoyl‐nucleobase hybrids in which the two moieties are linked by the carbonyl group [3]. As a continuation of our work concerning ferrocene‐labeled pyrimidine derivatives, in these study we report on regioselectivity of ferrocenoylation of uracil and its derivatives. To assess the optimized reaction condition, we selected the reaction of uracil with different acylation reagents in the presence of three bases (NaH, K2CO3 and Et3N) as a model reaction (Figure 1). The effect of various solvents (DMF and CH3CN) and temperatures of deprotection/coupling reactions on the model reaction will be also investigated. 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).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

POVEZANOST RADA