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Issue 15, 2018
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C5-Morpholinomethylation of N1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction

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Abstract

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.

Graphical abstract: C5-Morpholinomethylation of N1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction

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Article information


Submitted
30 Jan 2018
Accepted
15 Mar 2018
First published
15 Mar 2018

Org. Biomol. Chem., 2018,16, 2678-2687
Article type
Paper

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

J. Matić, I. Nekola, A. Višnjevac, R. Kobetić, I. Martin-Kleiner, M. Kralj and B. Žinić, Org. Biomol. Chem., 2018, 16, 2678
DOI: 10.1039/C8OB00253C

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