A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

• Ksenia Malkova,
• Andrey Bubyrev,
• Vasilisa Krivovicheva,
• Dmitry Dar’in,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

• [12], glycogen phosphorylase inhibitor 12 [13], MK2 kinase inhibitor 13 [14], ENL YEATS domain inhibitor 14 for leukemia treatment [15] and hepatitis C NS5B polymerase inhibitor 15 [16] (scaffold B, Figure 2). The very fact that it was impossible to isolate intermediate 4a from the reaction depicted

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

• Danny Lainé,
• Vincent Denavit,
• Olivier Lessard,
• Laurie Carrier,
• Charles-Émile Fecteau,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2020, 16, 2880–2887, doi:10.3762/bjoc.16.237

• were involved, among other things [5], in binding with UDP-Gal mutase [14], immunoglobulin [15][16], and glycogen phosphorylase [17]. The synthesis of complex polyfluorinated carbohydrates is challenging and new synthetic methods must be developed. Pioneering work by many groups brought significant

3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors

• Marion Donnier-Maréchal,
• David Goyard,
• Vincent Folliard,
• Tibor Docsa,
• Pal Gergely,
• Jean-Pierre Praly and
• Sébastien Vidal

Beilstein J. Org. Chem. 2015, 11, 499–503, doi:10.3762/bjoc.11.56

• phosphorylase; oxadiazole; Vilsmeier salt; Introduction Glycogen phosphorylase (GP) is a homodimeric enzyme that is responsible for the depolymerization of glycogen into glucose-1-phosphate, which is further converted into glucose delivered into the blood stream [1][2]. The control of GP activity could find

• explanation regarding the non-reactivity observed for this substrate. Enzymatic inhibition studies (RMGPb) The seven 3-glucosyl-5-amino-1,2,4-oxadiazoles 5a–e and 7a,b were evaluated as GP inhibitors using rabbit muscle glycogen phosphorylase b (RMGPb) as the model enzyme (see Supporting Information File 1

• ’-dialkylcarbodiimides or Vilsmeier salts. The 5-amino group introduced on the oxadiazole scaffold was expected to provide better inhibition of GP through potential additional interactions with the enzyme’s catalytic site; however, no inhibition was observed at 625 µM. Keywords: amidoxime; carbodiimide; glycogen

Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

• Miroslav Murár,
• Gabriela Addová and
• Andrej Boháč

Beilstein J. Org. Chem. 2013, 9, 173–179, doi:10.3762/bjoc.9.20

• kinase 1, alpha and beta adrenoreceptors, glycogen phosphorylase, IMP dehydrogenase, MMPs 2, 3, 9 and 13, etc. [1]. Vascular endothelial growth factor (VEGF-A) is a homodimeric glycoprotein and thought to be the key signalling molecule of angiogenesis, i.e., the formation of new blood vessels from pre