Naslov
C5-Morpholinomethylation of N1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction

Autori
Matić, Josipa ; Nekola, Irena ; Višnjevac, Aleksandar ; Kobetić, Renata ; Martin-Kleiner, Irena ; Kralj, Marijeta ; Žinić, Biserka

Izvornik
Organic & biomolecular chemistry (1477-0520) 16 (2018), 15; 2678-2687

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Cytosine, Morpholine, N1-sulfonylcytosine, 5-morpholinomethylcytosine, Aminomethylation, Morpholinomethylation, Mannich reaction

Sažetak
A fast and efficient route for the introduction of a methylene bridged-amine (morpholinomethyl) functionality in the C5 position of the sulfonylated cytosine nucleobase has been developed. First, novel N1-sulfonylcytosine derivatives 3–6 were prepared by the condensation of silylated cytosine with selected sulfonyl chlorides. They were subsequently transformed to 5-morpholinomethyl- N1-sulfonylcytosine derivatives (8, 12–15) using microwave irradiation. As a result of cytosine ring opening in N1-tosylcytosine, depending on the reaction conditions, peculiar tosyl-urea derivative 9 has been isolated, which provided additional insight into the reaction pathway. The influence of the C5- substituent on the antiproliferative activity has been evaluated by performing the MTT test on U251, MCF-7 and MOLT-4 tumor cell-lines.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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