Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

Foitzik, Richard C.; Devine, Shane M.; Hausler, Nicholas; Scammells, Peter J.

doi:10.1016/j.tet.2009.08.057

Cited by 15 publications

(15 citation statements)

References 16 publications

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“…All compounds were of Ͼ 95 % purity. 2Ј,3Ј,5Ј-Tri-O-acetylguanosine (1b), [13] 2Ј,3Ј,5Ј-O-(tert-butyldimethylsilyl)guanosine (1c), [14] 2Ј,3Ј-O-isopropylideneguanosine (1d) [3] and 2Ј,3Ј-O-isopropylideneguanosine-5Ј-N-ethylcarboxamide (1f) [3] were synthesised as previously published. Guanosine (1a) was purchased from Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

“…This generally requires numerous steps with incorporation of the 2-halo group occurring via stannylation [1] before nucleophilic substitution can take place at the 6-position from either chloro [2] or O 6 -(benzotriazol-1-yl) [3] moieties. However, protection of the hydroxy groups, as well as modifications to the 5Ј-position of the ribose also needed to be undertaken thereby increasing the sequence as well.…”

Section: Introductionmentioning

confidence: 99%

“…For a number of years, the versatility and efficiency of phosphonium-mediated coupling of tautomerizable heterocycles, [6] in particular nucleosides, has generated widespread attention. [7][8][9][10][11][12] Previous work by Lakshman et al [11] as well as our group [3] has shown that it is possible to convert certain protected guanosine derivatives to the corresponding O 6 -(benzotriazol-1-yl)guanosines using BOP and DBU. More specifically, TBS-protected guanosine was found to undergo this conversion in 65 % yield, while 2Ј,3Ј-isopropylidene-protected guanosine-5Ј-N-ethylcarboxamide gave a 95 % yield of the corresponding O 6 -(benzotriazol-1-yl) derivative.…”

Section: Introductionmentioning

confidence: 99%

“…This observation of aqueous uptake and poor solubility of inosine was also noted by Bae et al [8] This outcome is comparable to the previously reported reaction between TBS-protected guanosine and BOP in the presence of DBU (59 % vs. 65 % yield). [11] [3] [a] Isolated yield after chromatography.…”

Section: Introductionmentioning

confidence: 99%

“…These guanosine deriv-atives were prepared as described previously, [3,13,14] except in the case of 1e which was synthesized in an analogous fashion to 1f. [3] Although, these reactions succeeded in NMP, higher yields were obtained when MeCN was used as the reaction solvent. The difference was particularly significant in the case of 2b (74 % in NMP and 90 % in MeCN) and 2e (55 % in NMP and 92 % in MeCN).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Utility of 2‐Halo‐O⁶‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Devine¹,

Scammells²

2010

Eur J Org Chem

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An efficient synthesis of 2‐halo‐O6‐(benzotriazol‐1‐yl)‐substituted purine nucleosides has been accomplished via (benzotriazol‐1‐yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP)‐mediated coupling and subsequent halogenation via diazotization of the 2‐amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2‐ and 6‐positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and Utility of 2‐Halo‐O⁶‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Devine¹,

Scammells²

2010

Eur J Org Chem

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Evidence for the Existence of a Specific G Protein‐Coupled Receptor Activated by Guanosine

et al. 2011

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Guanosine, released extracellularly from neurons and glial cells, plays important roles in the central nervous system, including neuroprotection. The innovative DELFIA Eu-GTP binding assay was optimized for characterization of the putative guanosine receptor binding site at rat brain membranes by using a series of novel and known guanosine derivatives. These nucleosides were prepared by modifying the purine and sugar moieties of guanosine at the 6- and 5'-positions, respectively. Results of these experiments prove that guanosine, 6-thioguanosine, and their derivatives activate a G protein-coupled receptor that is different from the well-characterized adenosine receptors.

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Synthesis of Photoreactive 2‐Phenethylamine Derivatives – Synthesis of Adenosine Derivatives Enabling Functional Analysis of Adenosine Receptors by Photoaffinity Labeling

et al. 2013

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Abstract2‐Phenylethylamine is well known as a substructure of many biologically active compounds, and the synthesis of its photoreactive derivatives to allow the analysis of biological functions is reported. This allowed us to synthesise ligands for adenosine receptors, which have many functional roles in biology and have been extensively studied for their many roles in maintaining homeostasis. Adenosine is one of the most common biochemical compounds, but photoaffinity labeling has not yet been used to study adenosine receptors. Synthetic methods for producing photoreactive adenosine derivatives that can be used with adenosine receptors were established for the photophores phenyl azide and benzophenone. The effect of the introduction of the photoreactive components was determined using an adenosine receptor assay.

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Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

Cited by 15 publications

References 16 publications

Synthesis and Utility of 2‐Halo‐O⁶‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Synthesis and Utility of 2‐Halo‐O⁶‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Evidence for the Existence of a Specific G Protein‐Coupled Receptor Activated by Guanosine

Synthesis of Photoreactive 2‐Phenethylamine Derivatives – Synthesis of Adenosine Derivatives Enabling Functional Analysis of Adenosine Receptors by Photoaffinity Labeling

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Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

Cited by 15 publications

References 16 publications

Synthesis and Utility of 2‐Halo‐O6‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Synthesis and Utility of 2‐Halo‐O6‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Evidence for the Existence of a Specific G Protein‐Coupled Receptor Activated by Guanosine

Synthesis of Photoreactive 2‐Phenethylamine Derivatives – Synthesis of Adenosine Derivatives Enabling Functional Analysis of Adenosine Receptors by Photoaffinity Labeling

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Product

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Synthesis and Utility of 2‐Halo‐O⁶‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides

Synthesis and Utility of 2‐Halo‐O⁶‐(benzotriazol‐1‐yl)‐Functionalized Purine Nucleosides