Expeditious synthesis and biological evaluation of new C-6 1,2,3-triazole adenosine derivatives A1 receptor antagonists or agonists

Azolylpurines and azolylpurine nucleosides have important medicinal and biological applications. They are used as adenosine receptor agonists and antagonists and also as antivirals. Several compounds of this class exhibit fluorescent properties that can be applied in biological chemistry. This review summarizes and classifies all reported classes of purine‐azole conjugates, strategies for their syntheses, and suggestions of compound classes yet to be synthesized. Synthetic methodologies directed towards purine–azole conjugates, including SNAr reactions, cyclizations of amino‐ or hydrazinylpurines, and transition‐metal‐catalyzed cross‐coupling reactions, are discussed, as well as the use of selected azolylpurine derivatives as synthetic intermediates.

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“…[47] A variety of C(6)-1,2,3-triazolyl-substituted adenosine derivatives were synthesized and tested for A 1 receptor activity.…”

Section: Copper-catalyzed Azide-alkyne Cycloaddition (Cuaac) Approachmentioning

confidence: 99%

Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

2015

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“…EXPERIMENTAL SECTION 1 H-NMR and 13 C-NMR spectra were recorded at 300 MHz and 600 MHz and at 75.5 MHz and 100 MHz, respectively. The proton signals for residual non-deuterated solvents (δ 7.26 for CDCl 3 and δ 2.50 for DMSO-d 6 ) and carbon signals (δ 77.1 for CDCl 3 and δ 39.5 for DMSO-d 6 ) were used as internal references for 1 H-NMR and 13 C-NMR spectra, respectively. Coupling constants are reported in Hz.…”

Section: Discussionmentioning

confidence: 99%

“…For example, the groups of Van Calenbergh [2], Aldrich [3] and Lakshman [4] develop approaches to the synthesis of 2-triazolyl derivatives. On the other hand, 6-triazolyl derivatives have been studied by Lakshman and co-workers [5] and by the groups of Guieu and Parrain [6]. Moreover, fluorescent 8-triazolyl adenosine has been developed by the group of Grøtli.…”

mentioning

confidence: 99%

The Synthesis and X-ray Studies of 6-pyrrolidinyl-2-triazolyl Purine Arabinonucleoside

Novosjolova

Bizdēna

Belyakov

et al. 2013

Material Science and Applied Chemistry

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Abstract. C(6)-Pyrrolidinyl derivative with triazolyl moiety at C(2)-position was obtained from 2,6-bis-triazolylpurine arabinonucleoside via C(6)-regioselective nucleophilic substituon of 1,2,3-triazolyl moiety with pyrrolidine. The obtained compound was studied by NMR, X-ray, UV/VIS and emission spectra. Pyranose form of arabinose residue and α-configuration of the obtained compound were unambiguously proven by NMR and X-ray studies.

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“…Realizing that formation of the tetrazolyl tautomer was a potential hindrance to the CuAAC, Mathew et al . decided to use a C6-chloro-protected purine as the substrate for the Sonogashira cross-coupling reaction with TMS-acetylene to introduce a C6-acetylene ( 30 , Scheme 8 ) [ 96 ]. The result of this alternative synthetic strategy coupled with the CuAAC lead to the discovery of several different triazole-modified derivatives such as the homo-purine dimer compound 31 .…”

Section: Click Modification Of Nucleic Acidsmentioning

confidence: 99%

Chemical Architecture and Applications of Nucleic Acid Derivatives Containing 1,2,3-Triazole Functionalities Synthesized via Click Chemistry

2012

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There is considerable attention directed at chemically modifying nucleic acids with robust functional groups in order to alter their properties. Since the breakthrough of copper-assisted azide-alkyne cycloadditions (CuAAC), there have been several reports describing the synthesis and properties of novel triazole-modified nucleic acid derivatives for potential downstream DNA- and RNA-based applications. This review will focus on highlighting representative novel nucleic acid molecular structures that have been synthesized via the “click” azide-alkyne cycloaddition. Many of these derivatives show compatibility for various applications that involve enzymatic transformation, nucleic acid hybridization, molecular tagging and purification, and gene silencing. The details of these applications are discussed. In conclusion, the future of nucleic acid analogues functionalized with triazoles is promising.

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Expeditious synthesis and biological evaluation of new C-6 1,2,3-triazole adenosine derivatives A1 receptor antagonists or agonists

Cited by 19 publications

References 43 publications

Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

The Synthesis and X-ray Studies of 6-pyrrolidinyl-2-triazolyl Purine Arabinonucleoside

Chemical Architecture and Applications of Nucleic Acid Derivatives Containing 1,2,3-Triazole Functionalities Synthesized via Click Chemistry

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