Literature DB >> 1738143

Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues.

K Krohn1, H Heins, K Wielckens.   

Abstract

The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected via the isopropylidene compound 33. In contrast to the benzoic acid riboside (28) the benzamide riboside (2) showed extremely high cytotoxicity at nanomolar concentrations to S49.1 lymphoma cells but only slightly increased dexamethasone toxicity.

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Year:  1992        PMID： 1738143     DOI： 10.1021/jm00081a012

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  3 in total

1.  Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside.

Authors:  Rebecca R Midtkandal; Philip Redpath; Samuel A J Trammell; Simon J F Macdonald; Charles Brenner; Marie E Migaud
Journal:  Bioorg Med Chem Lett       Date:  2012-06-28       Impact factor: 2.823

2.  Synthesis of Stable NAD+ Mimics as Inhibitors for the Legionella pneumophila Phosphoribosyl Ubiquitylating Enzyme SdeC.

Authors:  Jerre M Madern; Robbert Q Kim; Mohit Misra; Ivan Dikic; Yong Zhang; Huib Ovaa; Jeroen D C Codée; Dmitri V Filippov; Gerbrand J van der Heden van Noort
Journal:  Chembiochem       Date:  2020-06-16       Impact factor: 3.164

Review 3.  Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides.

Authors:  Kartik Temburnikar; Katherine L Seley-Radtke
Journal:  Beilstein J Org Chem       Date:  2018-04-05       Impact factor: 2.883
  3 in total

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