Heterocyclic analogs of 5,12-naphthacenequinone 16. Synthesis and properties of new DNA ligands based on 4,11-diaminoanthra[2,3-b]thiophene-5,10-dione
A divergent route for the synthesis of new derivatives of 4,11-diaminoanthra[2,3- b ]thiophene-5,10-dione was developed based on the introduction of cyclic amines to the terminal positions of 4,11-aminoalkyl groups. Modification of the side chains of anthra[2,3- b ]-thiophene-5,10-dione increases th...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-06, Vol.56 (6), p.727-733 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 56 |
| creator | Andreeva, Daria V. Tikhomirov, Alexander S. Dezhenkova, Lyubov G. Kaluzhny, Dmitry N. Mamaeva, Olga K. Solovyova, Svetlana E. Sinkevich, Yuri B. Shchekotikhin, Andrey E. |
| description | A divergent route for the synthesis of new derivatives of 4,11-diaminoanthra[2,3-
b
]thiophene-5,10-dione was developed based on the introduction of cyclic amines to the terminal positions of 4,11-aminoalkyl groups. Modification of the side chains of anthra[2,3-
b
]-thiophene-5,10-dione increases the affinity of ligands to DNA duplex and decreases the affinity to G-quadruplexes. An analysis of the structure–activity relationship showed that 2-(piperidin-1-yl)ethylamine is the most promising side chain fragment for the development of new double-stranded DNA ligands. The ability of new ligands to bind to DNA duplex correlates with inhibition of tumor cell growth, which indicates the prospects for a further search for new antitumor compounds or chemical probes for duplex-forming nucleic acid sequences among 4,11-diaminoanthra[2,3-
b
]thiophene-5,10-diones. |
| doi_str_mv | 10.1007/s10593-020-02723-3 |
| format | Article |
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| subjects | Affinity Amines Analysis Chains Chemical compounds Chemistry Chemistry and Materials Science Deoxyribonucleic acid Diketones DNA Genetic research Heterocyclic compounds Ligands Organic Chemistry Pharmacy Synthesis Thiophene |
| title | Heterocyclic analogs of 5,12-naphthacenequinone 16. Synthesis and properties of new DNA ligands based on 4,11-diaminoanthra[2,3-b]thiophene-5,10-dione |
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