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

Matić, Josipa; Nekola, Irena; Višnjevac, Aleksandar; Kobetić, Renata; Martin-Kleiner, Irena; Kralj, Marijeta; Žinić, Biserka (2018) C5-Morpholinomethylation of N1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction. Organic & Biomolecular Chemistry, 16 (15). pp. 2678-2687. ISSN 1477-0520

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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.

Item Type: Article
Uncontrolled Keywords: Cytosine; Morpholine; N1-sulfonylcytosine; 5-morpholinomethylcytosine; Aminomethylation; Morpholinomethylation; Mannich reaction
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
NATURAL SCIENCES > Biology > Biochemistry and Molecular Biology
Divisions: Division of Molecular Medicine
Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida-Biserka Žinić098-0982914-2935MZOS
Višenamjensko očitavanje DNA / RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSenseIvo PiantanidaIP-2013-11-1477HRZZ
Depositing User: Josipa Matić
Date Deposited: 19 Apr 2018 08:52
Last Modified: 19 Apr 2018 08:52
URI: http://fulir.irb.hr/id/eprint/4015
DOI: 10.1039/C8OB00253C

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