Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C[sbnd]H bond functionalization
Treatment of toyocamycin or sangivamycin with 1,3-dibromo-5,5-dimethylhydantoin in MeOH (rt/30?min) gave 8-bromotoyocamycin and 8-bromosangivamycin in good yields. Nucleophilic aromatic substitution of 8-bromotoyocamycin with sodium azide provided novel 8
Kavoosi, Sam,Rayala, Ramanjaneyulu,Walsh, Brenna,Barrios, Maria,Gonzalez, Walter G.,Miksovska, Jaroslava,Mathivathanan, Logesh,Raptis, Raphael G.,Wnuk, Stanislaw F.
supporting information
p. 4364 - 4367
(2016/09/13)
Exploiting Protein Conformational Change to Optimize Adenosine-Derived Inhibitors of HSP70
HSP70 is a molecular chaperone and a key component of the heat-shock response. Because of its proposed importance in oncology, this protein has become a popular target for drug discovery, efforts which have as yet brought little success. This study demonstrates that adenosine-derived HSP70 inhibitors potentially bind to the protein with a novel mechanism of action, the stabilization by desolvation of an intramolecular salt-bridge which induces a conformational change in the protein, leading to high affinity ligands. We also demonstrate that through the application of this mechanism, adenosine-derived HSP70 inhibitors can be optimized in a rational manner.
Cheeseman, Matthew D.,Westwood, Isaac M.,Barbeau, Olivier,Rowlands, Martin,Dobson, Sarah,Jones, Alan M.,Jeganathan, Fiona,Burke, Rosemary,Kadi, Nadia,Workman, Paul,Collins, Ian,Van Montfort, Rob L. M.,Jones, Keith
p. 4625 - 4636
(2016/06/09)
Pyrrolopyrimidine nucleosides. 3. The total synthesis of toyocamycin, sangivamycin, tubercidin, and related derivatives.
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Tolman,Robins,Townsend
p. 2102 - 2108
(2007/10/04)
Pyrrolo[2,3-d]pyrimidine nucleoside antibiotics. Total synthesis and structure of toyocamycin, unamycin B, vengicide, antibiotic E-212, and Sangivamycin (BA-90912).
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Tolman,Robins,Townsend
p. 524 - 526
(2007/10/07)
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