Regioselective alkylation reaction of the 2′-deoxyctidine with 9-aminomethyl derivatives of SN38
| Autor: | Lech Kozerski, Robert Kawęcki, Elżbieta Bednarek, Jerzy Sitkowski, Wojciech Bocian, Beata Naumczuk |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Stereochemistry Chemical shift Organic Chemistry Regioselectivity Biological activity Topoisomerase-I Inhibitor Alkylation 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Cancer cell Deoxycytidine Spectroscopy DNA |
| Zdroj: | Journal of Molecular Structure. 1176:298-302 |
| ISSN: | 0022-2860 |
| Popis: | We present first evidence of a spontaneous alkylation of the 2′-deoxycytidine by potential topoisomerase I inhibitors from camptothecins family. The 7-ethyl-9-(N-morpholino)methyl-10-hydroxycamptothecin and the 7-ethyl-9-(N-pyrrolidinyl)methyl-10-hydoxycamptothecin regioselectively alkylate spontaneously an exo-cyclic nitrogen (N4) of the 2′- deoxycytidine. Product of the reaction has been confirmed using NMR techniques and DFT calculation of the carbon chemical shifts. This is the first evidence of spontaneous alkylation of DNA building block, the 2′-deoxycytidine, by this class of compounds, which are biologically active in vitro against several cancer cells, but tolerate normal cells. |
| Databáze: | OpenAIRE |
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