Synthesis and Fluorescent Properties of N(9)-Alkylated 2-Amino-6-Triazolylpurines and 7-Deazapurines
The Beilstein Journal of Organic Chemistry 2019
Andrejs Šišuļins, Jonas Bucevičius, Yu-Ting Tseng, Irina Novosjolova, Kaspars Traskovskis, Ērika Bizdēna, Huan-Tsung Chang, Sigitas Tumkevičius, Māris Turks

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.

Atslēgas vārdi
7-deazapurines; fluorescence; nucleophilic aromatic substitution; purines; push–pull systems; pyrrolo[2,3-d]pyrimidines

Šišuļins, A., Bucevičius, J., Tseng, Y., Novosjolova, I., Traskovskis, K., Bizdēna, Ē., Chang, H., Tumkevičius, S., Turks, M. Synthesis and Fluorescent Properties of N(9)-Alkylated 2-Amino-6-Triazolylpurines and 7-Deazapurines. The Beilstein Journal of Organic Chemistry, 2019, Vol. 15, 474.-489.lpp. e-ISSN 1860-5397. Pieejams: doi:10.3762/bjoc.15.41

Publikācijas valoda
English (en)
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