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Search for "antiviral activity" in Full Text gives 53 result(s) in Beilstein Journal of Organic Chemistry.
Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides
Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65
- analogous D-ribonolactones. C. Masked C-nucleoside monophosphates exhibiting potent antiviral activity and clinical utility. Pyrrolo- and imidazo[2,1-f][1,2,4]triazine C-nucleosides. A series of sugar- and nucleobase-substituted C-nucleosides were synthesized via nucleophilic substitution of D-ribonolactone
Synthetic mRNA capping
Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274
- can be transferred onto the diphosphate end of an RNA transcript to form a ribavirin-pppN structure. RNA transcripts blocked with ribavirin showed little translational efficiency, which might explain the antiviral activity of ribavirin [44]. Enzymatic formation of cap analogues from GTP analogues was
Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
Beilstein J. Org. Chem. 2017, 13, 1039–1049, doi:10.3762/bjoc.13.103
- a multitude of biological activities. The most famous representative of this family, cycloheximide (5), has been used for decades as an inhibitor of eukaryotic translation elongation [1][2][3]. Other members of this family show potent cell migration inhibition and antiviral activity [4][5][6], which
A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy
Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82
- ], and antitumor activities [11]. For example, the natural alkaloids berberine (IV) and narciclasine (V) possess antiplasmodial and antiviral activity, respectively [12][13]. Indotecan (VI) and its analog idimitecan (VII) were identified as topoisomerase I inhibitors, and were promoted into phase I
Synthesis of ribavirin 2’-Me-C-nucleoside analogues
Beilstein J. Org. Chem. 2017, 13, 755–761, doi:10.3762/bjoc.13.74
- promising as an anticancer drug [1][2][3]. The antiviral activity of ribavirin is ascribed to a combination of different mechanisms [4]. Although RBV causes some side effects [5][6][7] essentially due to its accumulation in red blood cells, it is indispensable in the treatment against hepatitis C virus (HCV
- if a bulkier ethyl group is used [16]. On the other hand, currently 2’-deoxy-2’-C-methyl-2’-C-fluoronucleosides are developed because a fluoro substituent in the 2’-position increases the antiviral activity and specificity due to a higher tolerance of viral polymerases with respect to incorporation
Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues
Beilstein J. Org. Chem. 2017, 13, 251–256, doi:10.3762/bjoc.13.28
- compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity. Keywords: analogue; antiviral; carbocyclic; nucleoside; phosphonate; Introduction Biomass is a valuable resource in search of renewable organic carbon
Interactions between cyclodextrins and cellular components: Towards greener medical applications?
Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261
Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases
Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254
- antiviral activity in various experiments [15][16][17][18][19][20][21][22]. Regarding the chemical synthesis of this class of pyrimidine nucleosides various approaches were published (see, e.g., [8][9][10][11][14][15][16][23][24]; reviewed by Vorbrüggen and Ruh-Pohlenz [25]). On the contrary, only few
The direct oxidative diene cyclization and related reactions in natural product synthesis
Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200
- Laurentia venustra and exhibited antiviral activity against vesicular stomatitis virus (VSV) and herpes simplex virus type 1 (HSV-1) [157]. Hashimoto et al. reported a total synthesis of the natural product in 1988 [158][159] employing a vanadium-catalyzed epoxidation as a key step in the stereoselective
Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208
- pharmacologic activities were reported for them. Thus, cholesterol-conjugated C-peptides, for example IV, are potent inhibitors of the Ebola virus glycoprotein-mediated cell entry [16], while cholesterol-derived amines exhibited a strong antiviral activity against the influenza A virus (IFV). These amines were
Potential of acylated peptides to target the influenza A virus
Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65
- Blocker” (EB) (Jones et al. 2006), with respect to their antiviral activity against infection by Influenza A Virus (IAV) H3N2. However, while this strategy seems at a first glance promising, the native situation is quite different from our experimental model settings. First, we found a strong potential of
- rather broad antiviral activity among several influenza strains in the micromolar range [14]. It has been shown that EB can bind to HA, and causes viral aggregation, which has been ascribed to multimerization of EB monomers providing a multivalent surface [15][16]. However, the inhibitory mechanism has
- supramolecular assembly, which allows multivalent interactions. By that, multivalent inhibitors could be designed with antiviral activity in the low micromolar range. Recently, we identified an antiviral peptide, which we derived from the paratope region of an antibody directed against HA binding to the sialic
The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles
Beilstein J. Org. Chem. 2015, 11, 385–391, doi:10.3762/bjoc.11.44
- atom from the other substrates (in our case, from 5-AT) to yield 2-aminopyrimidines 4a,b. In addition, the counter synthesis of pyrimidines 4a,b was realized by the reaction of esters 1a,b with guanidine carbonate under similar conditions (Scheme 2). Earlier, pyrimidine 4a that exhibited antiviral
- activity against HSV-1 was obtained by cyclization of ethyl 2-dimethylaminomethyliden-4,4,4-trifluoroacetoacetate [27]. The formation of 2-(tetrazolylamino)pyrimidine 5 is the result of nucleophilic substitution of the azide group in intermediate 2a by the aminotetrazole fragment, as the azide group is a
C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation
Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38
- of 5.0–40 μM. The synthesized compounds do not show any antiviral activity. Keywords: antitumor activity; click chemistry; 1,3-dipolar cycloaddition; nucleic acids; 2’-oxa-3’-aza-4’a-carbanucleoside analogs; Introduction Synthetic modified nucleosides are of great interest as potential new lead
- ][23][24][25][26][27]. 2’-Oxa-3’-aza-4’a-carbanucleosides 1–4 can be considered as mimics of natural nucleosides and act as terminators of the viral DNA chain. Their antiviral activity is linked to the competitive reversible inhibition of the reverse transcriptase. Furthermore, as antimetabolites, they
- inhibit cell proliferation of Vero, BS-C-1, HEp-2, MDCK, and HFF cells by 50% (CC50) at concentrations in the range of 5.0–40.0 μM. No antiviral activity against both RNA and DNA viruses was observed. Results and Discussion Chemistry The synthetic route to 5’-triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides
Recent advances in the electrochemical construction of heterocycles
Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303
- [65]. These structures consist of a terpene element and a benzodihydropyran unit and feature antiviral activity. First, quinomethane intermediate 53 is formed upon indirect anodic oxidation of 52, which reacts with α-phellandrene at room temperature to give compound 54. Alternatively, 53 can be
Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens
Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273
Pyrrolidine nucleotide analogs with a tunable conformation
Beilstein J. Org. Chem. 2014, 10, 1967–1980, doi:10.3762/bjoc.10.205
- acyclic compounds 1a–c are currently in clinical use for the treatment of diseases caused by DNA viruses and retroviruses. Cyclic analogs 2 and 3 were reported to exhibit antiviral activity against HIV strains [3]. These examples show that the modification of the sugar-phosphate moiety in nucleotides is a
Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium
Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140
- formed PG II aggregates, their properties, however, differ from those of the corresponding tri- and tetraantennary oligoglycines. In particular, the tendency to aggregate starts from Gly4 motifs instead of Gly7. The antiviral activity of end-glycosylated peptides was studied, and all capable of
- biantennary oligoglycines to assemble in aqueous media as well as the antiviral activity of glycoderivatives. Study of biantennary oligoglycines association in solution by dynamic light scattering The size of the particles formed by the biantennary oligoglycines in solution was measured with the dynamic light
- 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
Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs
Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136
- to improve HIV drug treatment and prevention. In this scenario, gold nanoparticles are an interesting chemical tool to design and prepare smart and efficient drug-delivery systems. Here we describe the preparation and antiviral activity of carbohydrate-coated gold nanoparticles loaded with anti-HIV
- -containing glyconanoparticles were characterized and the pH-mediated release of the drug from the nanoparticle has been determined. The antiviral activity was tested by evaluating the replication of NL4-3 HIV in TZM-bl infected cells. The proof-of-principle presented in this work aims to introduce gold
- the improvement of the solubility in water and biological media of the drugs and the improvement of cellular uptake due to the presence of carbohydrates on the GNPs. In addition a local increase of the drug concentration on the gold surface could also improve their antiviral activity. We reasoned that
Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach
Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9
- bisamides such as odorine, dehydroodorine and odorinol exhibited cytotoxic and antiviral activity [5]. There is only a limited number of putrescine bisamides isolated from natural sources and the amount of synthetic approaches known for these structurally interesting and biologically important molecules is
The chemistry of isoindole natural products
Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243
- interesting biological properties, such as high antiviral activity (156) [141], inhibition of the HIV-1 protease (157) [132], antibacterial and antifungal activities (159–160) [133] or neuritogenic properties (161) [134]. So far, only a few total syntheses were accomplished and the exact biosynthetic pathways
- are unknown. The sesquiterpenoid stachyflin (156) was first isolated from the fungus Stachybotrys sp. RF-7260 by Shionogi & Co., Ltd., Japan, in 1997 [130] and shows outstanding antiviral activity against the influenza A subtype H1N1 (IC50 = 3 nM), outperforming current drugs such as amantadine and
A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate
Beilstein J. Org. Chem. 2013, 9, 510–515, doi:10.3762/bjoc.9.55
- of various bioactive compounds that possess antibiotic, anti-inflammatory, antimicrobial [5], antidiabetic [6], and antiviral activity against retroviruses including HIV [7]. In addition, quinoxaline derivatives are also associated with a wide spectrum of biological effects including anticancer [8
Asymmetric synthesis of host-directed inhibitors of myxoviruses
Beilstein J. Org. Chem. 2013, 9, 197–203, doi:10.3762/bjoc.9.23
- University School of Medicine, 1510 Clifton Road, Atlanta, GA 30322, USA 10.3762/bjoc.9.23 Abstract High-throughput screening (HTS) previously identified benzimidazole 1 (JMN3-003) as a compound with broad antiviral activity against different influenza viruses and paramyxovirus strains. In pursuit of a lead
- compound from this series for development, we sought to increase both the potency and the aqueous solubility of 1. Lead optimization has achieved compounds with potent antiviral activity against a panel of myxovirus family members (EC50 values in the low nanomolar range) and much improved aqueous
- of the pure isomers for further pharmacokinetic and animal studies, we present here an asymmetric synthesis of 1 and its congeners with improved aqueous solubility and antiviral potency. Results and Discussion Design. We previously reported a series of compounds with antiviral activity against a
Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions
Beilstein J. Org. Chem. 2012, 8, 1814–1818, doi:10.3762/bjoc.8.207
- : Nitrated cubanes are remarkably explosive [3][4]; cubylamines possess antiviral activity [5]; and cubylamides have been shown to be P2X7 receptor antagonists [6]; whereas other cubane derivatives were examined as narcotic antagonists against both μ and ĸ receptors [7], as well as being monoamine oxidase
Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin
Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79
- need for new antiviral compounds. Starting from the natural, antivirally active compound glycyrrhizin, spacer-bridged derivatives were generated with improved antiviral activity against the influenza A virus infection. Simplified analogues of the triterpene saponin glycyrrhizin containing 1-thio-β-D
- cells, wherein the 3-(2-thioethyl)-N-acetylamino- and 3-(2-thioethyl)-thio-linked glucuronide derivatives were effective inhibitors with IC50 values as low as 54 µM. Keywords: antiviral activity; carbenoxolone; glycyrrhizin; influenza A virus; thioglycoside; triterpene; Introduction The triterpene
- ) and the hemisuccinate carbenoxolone (CBX), which showed CC50 values (half-maximal cytotoxic concentration) of 7.4 µM and 17.8 µM, respectively, none of the compounds tested were toxic at concentrations up to 250 µM. GL was not toxic at 2500 µM (Table 1). The antiviral activity of the compounds was
Marilones A–C, phthalides from the sponge-derived fungus Stachylidium sp.
Beilstein J. Org. Chem. 2011, 7, 1636–1642, doi:10.3762/bjoc.7.192
- serotonin receptors, and marilone B showed a specific antagonistic effect on the serotonin receptor 5-HT2B with a Ki value of 7.7 µM. Compounds 1–4 were further evaluated for antiviral activity, for inhibition of protein kinases and proteases, for growth inhibition of antibiotic-resistant Mycobacterium
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