Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

• Thierry Milcent,
• Pascal Retailleau,
• Benoit Crousse and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

• , the tetrahydropyridazines, six-atom nitrogenous heterocycles, are found in various bioactive molecules such as influenza virus neuraminidase inhibitors, GABA type A receptor modulators, and regulators of progesterone receptor or cannabinoid CB1 receptor antagonists (Figure 1) [6][7][8][9]. This

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• -Lysine binding [39]. Although PLP is not a reported neuraminidase inhibitor, its main interaction in the active site could be reasoned based on previous results with sialic acid-derived phosphonate analogues. In this regard, it has been suggested that the inhibition of different strains of influenza

• virus neuraminidase is due to a strong electrostatic interaction between the phosphonate group and the arginine pocket in the active site [40]. Conclusion A small series of anomeric 1,2,3-triazole-linked sialic acid derivatives was synthesised in good yields and high purity via CuAAC click chemistry and

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• -structural protein 1 (NS1A) homodimer (Figure 9) [64]. Protein NS1A is a highly conserved virulence factor from influenza virus (H3N2) comprised of an N-terminal double-stranded RNA (dsRNA)-binding domain (RBD) and a multifunctional C-terminal effector domain (ED), each of which can independently form

Leveraging glycomics data in glycoprotein 3D structure validation with Privateer

• Haroldas Bagdonas,
• Daniel Ungar and
• Jon Agirre

Beilstein J. Org. Chem. 2020, 16, 2523–2533, doi:10.3762/bjoc.16.204

• [2][3]; the level of N-glycan expression regulates the adhesiveness of a cell [4]; glycosylation also plays a role in immune function [5] and cellular signalling [5][6]. At the forefront, glycosylation plays a significant role in influencing protein–protein interactions. For example, the influenza

• virus uses the haemagglutinin glycoprotein to recognise and bind sialic acid decorations of human cells in the respiratory tract [7]. Glycosylation is also used by pathogens to evade the host’s immune system via glycan shields [8][9][10], and thereby to delay an immune response [11]. The structural

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

• Cloudius R. Sagandira and
• Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

• Tamiflu is currently one of the most important drugs available to combat the influenza virus and this has seen immense research efforts by the scientific community to exclusively focus on the development of new, better and practical approaches to manufacture this drug [1][2]. More than 60 synthetic routes

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• commercial ELISA plates and anti-carbohydrate antibodies were detected in the nanomolar range both using purified anti-HIV human monoclonal antibodies or serum from immunized mice against S. pneumoniae. Detection of carbohydrate–influenza virus interactions The SERS methodology was extended to the

• indicative of the successful binding [85]. In this field, a naturally occurring sialylglycopeptide extracted from egg yolks was converted into a thiol-terminated molecule and grafted on AuNPs, to develop a gold-based sensor for influenza virus detection, using both UV–vis spectroscopy and dynamic light

• scattering. Moreover, a selective detection of the influenza virus can be accomplished. Viral hemagglutinin (HA) protein, in fact, can bind selectively sialic acid residues, but the human influenza virus recognizes the sialic acid α(2,6)galactose sequence while the avian virus recognizes sialic acid α(2,3

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

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• , Germany 10.3762/bjoc.11.65 Abstract For antiviral drug design, especially in the field of influenza virus research, potent multivalent inhibitors raise high expectations for combating epidemics and pandemics. Among a large variety of covalent and non-covalent scaffold systems for a multivalent display of

• inhibitors, we created a simple supramolecular platform to enhance the antiviral effect of our recently developed antiviral Peptide B (PeBGF), preventing binding of influenza virus to the host cell. By conjugating the peptide with stearic acid to create a higher-order structure with a multivalent display, we

• could significantly enhance the inhibitory effect against the serotypes of both human pathogenic influenza virus A/Aichi/2/1968 H3N2, and avian pathogenic A/FPV/Rostock/34 H7N1 in the hemagglutination inhibition assay. Further, the inhibitory potential of stearylated PeBGF (C18-PeBGF) was investigated

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

• Roberto Romeo,
• Caterina Carnovale,
• Salvatore V. Giofrè,
• Maria A. Chiacchio,
• Adriana Garozzo,
• Emanuele Amata,
• Giovanni Romeo and
• Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

• (African green monkey kidney) for varicella-zoster virus (VZV); (e) Madin–Darby canine kidney (MDCK) for influenza virus A/Puerto Rico/8/34 H1N1 (PR8). Acyclovir was used as the reference compound. For the synthesized compounds, no inhibitory activity against any virus was detected until 250 μM. Biological

• antiviral assays the following viruses were used: Poliovirus 1 (Sabin strain: VR-1562), Human echovirus 9 (VR-1050), Herpes simplex type 1 (HSV-1: VR-260), Coxsackievirus B1 (VR-28), adenovirus type 2 (VR-1080), Cytomegalovirus (CMV: VR-538), varicella-zoster virus (VZV: VR-1367), influenza virus A/Puerto

Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

• Svetlana V. Tsygankova,
• Alexander A. Chinarev,
• Alexander B. Tuzikov,
• Nikolai Severin,
• Alexey A. Kalachev,
• Juergen P. Rabe,
• Alexandra S. Gambaryan and
• Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

• assembling glycopeptides demonstrated an antiviral potency which was up to 50 times higher than the activity of peptide-free glycans. Keywords: glycopeptides; influenza virus; multivalent glycosystems; oligoglycine; polyglycine II; self-assembling; tectomers; Introduction Recently, we have synthesized and

• structural motifs (core), where the antennae are connected to each other. The knowledge of the rules found for the unsubstituted assembly of oligoglycines may be suitable for us for the design of corresponding sialo derivartives, which are candidate therapeutics for the blocking of the influenza virus [6

• assembling of monomer layers into surface tectomer layers or into long-living associates in solution. 4) Oligoethylene glycol core ‘inhibits’ the association both in the liquid phase and on a mica surface. Antiviral activity of glycoderivatives The idea of antiadhesion influenza virus therapy is based on the

Asymmetric synthesis of host-directed inhibitors of myxoviruses

• Terry W. Moore,
• Kasinath Sana,
• Dan Yan,
• Pahk Thepchatri,
• John M. Ndungu,
• Manohar T. Saindane,
• Mark A. Lockwood,
• Michael G. Natchus,
• Dennis C. Liotta,
• Richard K. Plemper,
• James P. Snyder and
• Aiming Sun

Beilstein J. Org. Chem. 2013, 9, 197–203, doi:10.3762/bjoc.9.23

• attribute the assay discrepancy to the inherent variability in the assay system. While the compounds appear to be active against both influenza and measles virus, they are somewhat more active against the influenza virus strain (WSN) than against the measles virus. Among the compounds surveyed, (S)-14b is

Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin

• Christian Stanetty,
• Andrea Wolkerstorfer,
• Hassan Amer,
• Andreas Hofinger,
• Ulrich Jordis,
• Dirk Claßen-Houben and
• Paul Kosma

Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79

• , Austria Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria 10.3762/bjoc.8.79 Abstract The influenza virus infection remains a significant threat to public health and the increase of antiviral resistance to available drugs generates an urgent

• directed against a broad spectrum of viruses comprising herpes-, corona-, alpha-, and flaviviruses, HIV, Epstein–Barr virus, influenza A virus (IAV), vaccinia and polio type I viruses as examples [3][4][5][6][7][8]. In particular anti-influenza virus activities have been described, although the underlying

• exhibited no toxicity at concentrations up to 250 μM and significantly enhanced the anti-influenza virus activity of the natural triterpene glycoside glycyrrhizin. Structure of glycyrrhizin (GL), carbenoxolone (CBX), and spacer analogues. 400 MHz 1H NMR expansion plots of the carbohydrate region of compound