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 | ||||||||||||
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| 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 |
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| Divisions: | Division of Molecular Medicine Division of Organic Chemistry and Biochemistry Division of Physical Chemistry |
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| Depositing User: | Josipa Matić | ||||||||||||
| Date Deposited: | 19 Apr 2018 08:52 | ||||||||||||
| URI: | http://fulir.irb.hr/id/eprint/4015 | ||||||||||||
| DOI: | 10.1039/C8OB00253C |
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