Photochemistry of 6-amino-2-azido, 2-amino-6-azido and 2,6-diazido analogues of purine ribonucleosides in aqueous solutions

Komodziński, Krzysztof; Lepczyńska, Jolanta; Gdaniec, Zofia; Bartolotti, Libero J.; Delley, B.; Franzen, Stefan; Skalski, Bohdan

doi:10.1039/c3pp50385b

Cited by 8 publications

(4 citation statements)

References 43 publications

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“…[152][153][154] 6-Azidopurine 217 underwent photocatalytic degradation under UV irradiation via the formation of nitrene intermediate 218, followed by rearrangement to the seven-membered cyclic carbodiimide 219 and hydrolysis to triazepinone 220 (Scheme 34A). [155,156] Also, 2-azidopurines have been shown to undergo photocatalytic degradation in aerobic media, yielding seven-membered oxadiazepane 222 (Scheme 34B). [157] Purine Noxides, on the contrary, upon irradiation undergo slow pyrimidine ring cleavage at C-2 to aminoacetylimidazoles 224 and 225 (Scheme 34C).…”

Section: Ring Opening Of N-1-quaternized Purinesmentioning

confidence: 99%

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

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Purines, which are regarded as relatively stable heterocyclic systems, can be opened at both pyrimidine and imidazole rings. Purine ring opening also serves as a tool for the preparation of ring-modified purines through rearrangement/recyclization mechanisms. The obtained imidazole, pyrimidine, and purine derivatives are privileged molecular scaffolds in medicinal and agricultural chemistry. Purine ring-opening approach is a useful alternative for their synthesis, which competes well with de novo approach or modification of a conserved heterocyclic core. The substitution patterns and groups that activate purines towards ring opening are reviewed. Moreover, mechanistic studies using labelled substrates, which are leading to rearranged purine derivatives are covered. Furthermore, an insight into imidazole ring opening upon exposure of purine system to DNA damaging agents is provided.

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Section: Ring Opening Of N-1-quaternized Purinesmentioning

confidence: 99%

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

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“…In several cases chromatographic separation of the N(9)/(7) isomers was easier at the stage of diazido products 2a and 2a’ . Diazido products 2 are light and temperature sensitive [48], but can be stored without degradation in refrigerator at −20 °C for a prolonged period of time. In addition, DSC measurements for compounds 2a–c were done.…”

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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“…and CuSO 4 ‧5H 2 O (6 mol %). If sodium ascorbate is used in excess, the reduction of the second azido group is observed, yielding the 2,6‐diaminopurine derivative (Komodziński et al., 2014). If a Cu(I) source is not present, no reduction of the azido group takes place.…”

Section: Commentarymentioning

confidence: 99%

Synthesis of Azido and Triazolyl Purine Ribonucleosides

et al. 2021

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Here, we describe detailed synthetic protocols for preparation of 6amino/thio-2-triazolylpurine ribonucleosides. First, 9-(2 ,3 ,5 -tri-O-acetyl-β-D-ribofuranosyl)-2,6-diazido-9H-purine, to be used as a key starting material, is synthesized in an S N Ar reaction with NaN 3 starting from commercially available 9-(2 ,3 ,5 -tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine. Next, 2,6-bis-triazolylpurine ribonucleoside is obtained in a CuAAC reaction between diazidopurine derivative and phenyl acetylene, and used in S N Ar reactions with N-and S-nucleophiles. In these reactions, the triazolyl ring at the purine C6 position acts as a good leaving group. Cleavage of acetyl protecting groups from the ribosyl moiety is achieved in presence of piperidine. In the S N Ar reaction with amino acid derivatives, the acetyl groups remain intact. Moreover, 9-(2 ,3 ,5 -tri-O-acetyl-β-D-ribofuranosyl)-2,6-diazido-9H-purine is selectively reduced at the C6 position using a CuSO 4 •5H 2 O/sodium ascorbate system. This provides a straightforward approach for synthesis of 9-(2 ,3 ,5 -tri-O-acetyl-β-D-ribofuranosyl)-6-amino-2-azido-9H-purine.

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Photochemistry of 6-amino-2-azido, 2-amino-6-azido and 2,6-diazido analogues of purine ribonucleosides in aqueous solutions

Cited by 8 publications

References 43 publications

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

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

Synthesis of Azido and Triazolyl Purine Ribonucleosides

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