Synthesis of purine nucleoside—amino acid conjugates and their photophysical properties

Cīrule, Dace; Ozols, Kristers; Platnieks, Oskars; Bizdēna, Ērika; Māliņa, Ilze; Turks, Māris

doi:10.1016/j.tet.2016.05.043

Cited by 12 publications

(9 citation statements)

References 36 publications

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“…4,17–18 Studies with 7-azido-7-deazapurine nucleosides as well as 8-azido- or 8-alkynyl-7-deazapurine nucleosides have received much less attention due to the lack of availability of the convenient synthetic protocols for their synthesis. 17,19 This is despite the fact that azidonucleosides 20–22 including 8-azido as well as 8-alkynyl purine23 nucleosides have been used as convenient substrates for CuAAC and strain-promoted azide-alkyne cycloaddition (SPAAC). 24–26 This approach is rapidly growing field with various applications, including in vivo imaging, of azido/alkyne-modified nucleoside/nucleotides 26–27 or DNA/RNA fragment click adducts.…”

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confidence: 99%

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization

Kavoosi

Rayala

Walsh

et al. 2016

Tetrahedron Letters

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Treatment of toyocamycin or sangivamycin with 1,3-dibromo-5,5-dimethylhydantoin in MeOH (r.t./30 min) gave 8-bromotoyocamycin and 8-bromosangivamycin in good yields. Nucleophilic aromatic substitution of 8-bromotoyocamycin with sodium azide provided novel 8-azidotoyocamycin. Strain promoted click reactions of the latter with cyclooctynes resulted in the formation of the 1,2,3-triazole products. Iodine-mediated direct C8-H bond functionalization of tubercidin with benzotriazoles in the presence of tert-butyl hydroperoxide gave the corresponding 8-benzotriazolyltubercidin derivatives. The 8-(1,2,3-triazol-1-yl)-7-deazapurine derivatives showed moderate quantum yields and a large Stokes shifts of ~ 100 nm.

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confidence: 99%

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization

Kavoosi

Rayala

Walsh

et al. 2016

Tetrahedron Letters

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“…We have recently observed significant fluorescence in the triazolylpurine and triazolyl-7-deazapurine series [25,29,40–41]. Therefore, we developed synthetic methods that can provide structurally related chromophores of the purine and 7-deazapurine series possessing identical substitution pattern (structural congeners G and H , Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

Šišuļins

Bucevičius

Tseng

et al. 2019

Beilstein J. Org. Chem.

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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.

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“…Among the widely studied 1,2,3-triazolyl nucleoside conjugates [57,58], the synthesis of 2-triazolylpurine derivatives containing a designed substituent at C6 has been little discussed. 6-N-Substituted purines have been the most studied [11,[59][60][61][62], but 6-S- [14,63] or 6-O-analogues are less common [61].…”

Section: Introductionmentioning

confidence: 99%

“…Then, the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction provides the target product IV (Scheme 1, pathway A) [59][60][61]. Pathway B is designed on the basis of our group investigations on the synthesis of 2,6-bistriazolylpurine derivatives and their application in reactions with N-, S-and P-nucleophiles making use of regioselective S N Ar reactions at C(6) (V→VI→IV, Scheme 1) [11,14,62,63,77,78]. The main advantage of pathway B is a straightforward access to 2,6-diazidopurines V and 2,6-bistriazolylpurines VI due to excellent nucleophilic properties of the azide ion and wellestablished CuAAC reaction.…”

Section: Introductionmentioning

confidence: 99%

1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

Cīrule¹,

Novosjolova²,

Bizdēna³

et al. 2021

Beilstein J. Org. Chem.

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A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SNAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C–O and C–C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.

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Synthesis of purine nucleoside—amino acid conjugates and their photophysical properties

Cited by 12 publications

References 36 publications

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

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Synthesis of purine nucleoside—amino acid conjugates and their photophysical properties

Cited by 12 publications

References 36 publications

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

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1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles