| Title |
Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines / |
| Authors |
Šišuļins, Andrejs ; Bucevičius, Jonas ; Tseng, Yu-Ting ; Novosjolova, Irina ; Traskovskis, Kaspars ; Bizdēna, Ērika ; Chang, Huan-Tsung ; Tumkevičius, Sigitas ; Turks, Māris |
| DOI |
10.3762/bjoc.15.41 |
| Full Text |
|
| Is Part of |
Beilstein journal of organic chemistry.. Frankfurt am Main : Beilstein-Institut. 2019, vol. 15, p. 474-489.. ISSN 1860-5397 |
| Keywords [eng] |
7-deazapurines ; fluorescence ; nucleophilic aromatic substitution ; purines ; push–pull systems ; pyrrolo[2,3-d]pyrimidines |
| Abstract [eng] |
The synthesis of novel fluorescent N(9)-alkylated 2-amino-6-triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push–pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine heterocycles, which were additionally extended by triazole moieties, the compounds with electron-donating groups showed intramolecular charge transfer character (ICT/TICT) of the excited states which was proved by solvatochromic dynamics and supported by DFT calculations. In the 7-deazapurine series this led to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future. |
| Published |
Frankfurt am Main : Beilstein-Institut |
| Type |
Journal article |
| Language |
English |
| Publication date |
2019 |
| CC license |
|
