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

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

• Raphael Bereiter,
• Marco Oberlechner and
• Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

• , glycogen synthase kinase 3 (GSK-3), leucine-rich repeat kinase 2 (LRRK2), tyrosine phosphorylation-regulated kinase-1A (DYRK1A) and CDC2-like kinase 1 (CLK1), and fatty acid amide hydrolase (FAAH) [4]). Similar properties were ascertained for 1-deazapurine derivatives (imidazo[4,5-b]pyridines) and

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

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

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

• Takashi Go,
• Akane Morimatsu,
• Hiroaki Wasada,
• Genzoh Tanabe,
• Osamu Muraoka,
• Yoshiharu Sawada and
• Mitsuhiro Yoshimatsu

Beilstein J. Org. Chem. 2018, 14, 2722–2729, doi:10.3762/bjoc.14.250

• compounds operate by inhibiting proteins or enzymes that regulate cell cycles, including cyclin-dependent kinases [9], tyrosine kinase [10], glycogen-synthase kinase and mitochondrial malate dehydrogenase [11]. These interesting biological activities led us to develop one-pot sequential or cascade protocols

Kinetic analysis of mechanoradical formation during the mechanolysis of dextran and glycogen

• Naoki Doi,
• Yasushi Sasai,
• Yukinori Yamauchi,
• Tetsuo Adachi,
• Masayuki Kuzuya and
• Shin-ichi Kondo

Beilstein J. Org. Chem. 2017, 13, 1174–1183, doi:10.3762/bjoc.13.116

• , Japan 10.3762/bjoc.13.116 Abstract A detailed electron spin resonance (ESR) analysis of mechanically induced free radicals (mechanoradicals) formation of glucose-based polysaccharides, dextran (Dx) and glycogen (Gly) was performed in comparison with amylose mechanoradicals. The ESR spectra of the

• structure. Keywords: dextran; electron spin resonance (ESR); glycogen; mechanoradical; polysaccharide; Introduction There are many reports on the mechanolysis of synthetic and natural polymers. It is well-known that mechanically induced radicals, so-called mechanoradicals, are produced by the mechanolysis

• prodrugs produced as a prototype [19]. However, HEC is not metabolized by humans. Therefore if one could use a polymer metabolized by humans, such as Dx or glycogen (Gly), a promising graft polymeric prodrug could be obtained through a mechanochemical reaction in a totally dry process. It is necessary to

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• molecules composed of monosaccharide units coupled together via glycosidic linkages to form long linear or branched chains. Some of the most common polysaccharides found in nature include cellulose, starch, glycogen or chitin [49]. Upon hydrolysis, these structures break down into smaller fragments such as

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• are, with proteins and lipids, essential constituents of living organisms because they are key biological intermediates for energy storage. In autotrophs, such as plants, sugars are converted into starch whereas for heterotrophic organisms, such as animals, they are stored as glycogen. However

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

• 1918, F-69622, Villeurbanne, France Department of Medical Chemistry, Faculty of Medicine, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary 10.3762/bjoc.11.56 Abstract Glycogen phosporylase (GP) is a promising target for the control of glycaemia. The design of inhibitors binding at the

• ’-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

• 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

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

• Catalin V. Maftei,
• Elena Fodor,
• Peter G. Jones,
• M. Heiko Franz,
• Gerhard Kelter,
• Heiner Fiebig and
• Ion Neda

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

• glycogen synthase kinase 3 (GSK-3), a key regulator of both differentiation and cellular proliferation [9]. An alternative antitumor strategy involves the inhibition of processes involved in tumor growth, e.g., angiogenesis. Integrin αvβ3 is a receptor that has been found on the surface of many tumor cells

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• neuroprotection is to inhibit the signaling molecules that antagonize cellular survival and promote neuron death in disease models. Glycogen synthase kinase-3 (GSK-3) is an essential signaling molecule involved in many cellular processes including glycogen metabolism, cell-cycle regulation, cellular proliferation

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

Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

• Nikolay T. Tzvetkov,
• Harald Euler and
• Christa E. Müller

Beilstein J. Org. Chem. 2012, 8, 1584–1593, doi:10.3762/bjoc.8.181

• involved [3]. Recently, specifically substituted imidazo[1,5-f][1,2,4]triazines (4) have been developed as polo-like kinase (PLK) inhibitors with potential as anticancer therapeutics [10]. The 1,2,4-triazines 4 also exhibited inhibitory activities against glycogen synthase kinase 3 (GSK3β), and may