ArticleTetrahedron2008
Mechanistic studies in the synthesis of a series of thieno-expanded xanthosine and guanosine nucleosides.
Article in Tetrahedron, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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Who cites it
10 citing papers in PubMed.
- Novel tricycle expanded purine nucleosides with pan-viral activity.Bioorganic & medicinal chemistry · 2025Article
- An Expedient Synthesis of Flexible Nucleosides through Enzymatic Glycosylation of Proximal and Distal Fleximer Bases.Chembiochem : a European journal of chemical biology · 2020Article
- Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity.Molecules (Basel, Switzerland) · 2019Article
- The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold.Antiviral research · 2018Review
- Thiophene-expanded guanosine analogues of Gemcitabine.Bioorganic & medicinal chemistry letters · 2015Article
- Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.Bioorganic & medicinal chemistry · 2015Article
- Formal (4+1) cycloaddition of methylenecyclopropanes with 7-aryl-1,3,5-cycloheptatrienes by triple gold(I) catalysis.Angewandte Chemie (International ed. in English) · 2014Article
- Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines.Bioorganic & medicinal chemistry · 2014Article
- Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2'-deoxy nucleoside analogues.Bioorganic & medicinal chemistry · 2012Article
- Tricyclic 2'-C-modified nucleosides as potential anti-HCV therapeutics.Organic letters · 2010Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
During the synthetic pursuit of guanosine (triG) and xanthosine (triX) tricyclic nucleosides analogues, an interesting side product was discovered. In an effort to uncover the mechanistic factors leading to this result, a series of reaction conditions were investigated. It was found that by varying the conditions, the appearance of the side product could be controlled. In addition, the yield of the desired products could be manipulated to afford either a 50:50 mix of both triG and triX, or a majority of one or the other. To demonstrate the broad utility of the method, it was also adapted to the synthesis of guanosine and xanthosine from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxyamide (AICAR). The mechanistic details surrounding the synthetic efforts are reported herein.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.