scholarly journals 2′-Deoxyuridines with a 5-Heteroaromatic Substituent: Synthesis and Biological Evaluation

1995 ◽  
Vol 6 (4) ◽  
pp. 262-270 ◽  
Author(s):  
I. Luyten ◽  
L. Jie ◽  
A. Van Aerschot ◽  
C. Pannecouque ◽  
P. Wigerinck ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Biological Evaluation ◽  
Dipolar Cycloaddition ◽  
Cross Coupling Reaction ◽  
Simplex Virus ◽  
New Compounds ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of ◽  
Hsv 1

A series of novel 2′-deoxyuridines with a thienyl substituent in the 5-position were synthesized as potential anti-HSV-1 agents. The brominated derivatives (1d, 1e and 3b) were obtained via halogenation reactions of the protected 5-(thien-2-yl)-2′-deoxyuridine and 5-(thien-3-yl)-2′-deoxyuridine, respectively. The palladium-catalysed cross-coupling reaction with stannylated thiophene was used for the synthesis of ( E)-5-(2-thienylvinyl)-2′-deoxyuridine and 5-(5,2′-dithien-2-yl)-2′-deoxyuridine. These compounds show moderate to good activity against herpes simplex virus type 1 (HSV-1) in the order of decreasing activity 1d>4>1e>3b∼5. Finally, two substituted 5-isoxazol derivatives of 2′-deoxyuridine (6a and 6b) were obtained via a 1,3-dipolar cycloaddition of the protected 5-ethynyl-2′-deoxyuridine. These new compounds demonstrated poor affinity for the virus-specific enzyme thymidine kinase.

scholarly journals Synthesis and Biological Evaluation of Novel 2-Substituted ­Analogues of (–)-Pentenomycin I

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 475-481
Author(s):  
Stavroula A. Zisopoulou ◽  
Spyridon Bousis ◽  
Jörg Haupenthal ◽  
Jennifer Herrmann ◽  
Rolf Müller ◽  
...  
Keyword(s):  
Natural Product ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Eukaryotic Cell ◽  
Biological Evaluation ◽  
Gram Positive Bacteria ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

A library of novel 2-substituted derivatives of the antibiotic natural product pentenomycin I is presented. The new collection of analogues is divided in two main classes, 2-alkynyl- and 2-aryl- derivatives, which are accessed by the appropriate type of palladium-catalyzed cross-coupling reaction of the 2-iodo-protected pentenomycin I with suitable nucleophiles. The new derivatives were tested for their activity against certain types of bacteria and one of them, compound 8h, was found to exhibit significant inhibitory activity against several Gram-positive bacteria but also displayed cytotoxic activity against eukaryotic cell lines.

Design, synthesis and biological evaluation as immunosuppressant of amino alcohol derivatives containing thioether

2021 ◽  
Vol 11 (5) ◽  
pp. 773-780
Author(s):  
Yanjie Li ◽  
Yongqiang Li ◽  
Liu Yang ◽  
Zhi Liu ◽  
Ruimeng Zhang ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Coupling Reaction ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Suzuki Coupling Reaction ◽  
Sphingosine 1 Phosphate ◽  
Potential Activity ◽  
Key Steps ◽  
Synthesis And Biological Evaluation

To develop a safer immunosuppressant for organ transplantation and autoimmune disease treatment, in this study, several of novel amino alcohol derivatives containing thioether moiety were synthesized with 7-bromo-tetralin-2-one as starting material, and Suzuki coupling reaction and Bucherer-Bergs reaction as key steps. Their activity as sphingosine 1-phosphate receptor type 1 (S1P1) agonists were evaluated by [γ-35S] GTP binding assay. Among the thioether substituted compounds, compound 10 showed good activity as S1P1 agonist at low micromolar concentration (EC50 = 0.698 μmol/L). The result suggested that it has potential activity against autoimmune diseases and immunosuppressant of organ transplantations.

The convenient aqueous synthesis and biological evaluation of ortho-(3,4,5-trimethoxybenzoyl)-acetanilides as novel anti-cancer agents

RSC Advances ◽  
2014 ◽  
Vol 4 (78) ◽  
pp. 41510-41520 ◽  
Author(s):  
Jianfei Sheng ◽  
Fei Mao ◽  
Jun Yan ◽  
Ling Huang ◽  
Xingshu Li
Keyword(s):  
Polyethylene Glycol ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biological Evaluation ◽  
Pd Catalyst ◽  
Aqueous Synthesis ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Anti Cancer ◽  
Synthesis And Biological Evaluation

A series of new ortho-(3,4,5-trimethoxybenzoyl)-acetanilides were synthesised by the cross-coupling reaction catalyzed with Pd catalyst in aqueous medium, with polyethylene glycol as additive under very mild conditions.

scholarly journals Synthesis and Screening of Anti-HSV-1 Activity of Thioglucoside Derivatives of Natural Polyhydroxy-1,4-Naphthoquinones

2019 ◽  
Vol 14 (6) ◽  
pp. 1934578X1986067 ◽  
Author(s):  
Sergey G. Polonik ◽  
Natalia V. Krylova ◽  
Galina G. Kompanets ◽  
Olga V. Iunikhina ◽  
Yuri E. Sabutski
Keyword(s):  
Antiviral Activity ◽  
Radical Scavenging ◽  
Effective Inhibition ◽  
Infected Cells ◽  
Virucidal Effect ◽  
Simplex Virus ◽  
Derivatives Of ◽  
Hsv 1

Four 1,4-naphthoquinone dithioglucoside derivatives based on natural polyhydroxy-1,4-naphthoquinones were synthesized. These thioglucosides were screened for their antiradical and antiviral activity in vitro. Antiradical activity of tested compounds was determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay. The anti-herpes simplex virus type 1 (anti-HSV-1) activity of thioglucosides was analyzed by the cytopathic effect inhibition assay and mode of antiviral action was determined by the addition of the tested compounds to uninfected cells, to the virus prior to infection, or to herpes-infected cells. Most effective inhibition of HSV-1 replication was observed at pretreatment of virus by the compounds (direct virucidal effect). The dithioglucoside conjugate with the single β-OH group and lipophilic ethyl substituent in naphthoquinone core showed the greatest antiviral activity.

Nucleic acid related compounds. 53. Synthesis and biological evaluation of 2′-deoxy-β-threo-pentofuranosyl nucleosides. "Reversion to starting alcohol" in Barton-type reductions of thionocarbonates

1988 ◽  
Vol 66 (5) ◽  
pp. 1258-1262 ◽  
Author(s):  
Morris J. Robins ◽  
Danuta Madej ◽  
Fritz Hansske ◽  
John S. Wilson ◽  
Gilles Gosselin ◽  
...  
Keyword(s):  
Herpes Simplex Virus ◽  
Herpes Simplex ◽  
Nucleic Acid ◽  
Biological Evaluation ◽  
Subsequent Reduction ◽  
Reaction Sequence ◽  
Simplex Virus ◽  
Synthesis And Biological Evaluation ◽  
Related Compounds

Treatment of selectively 3′,5′-protected β-D-xylofuranosyl nucleosides (4) with phenyl chlorothionocarbonate and DMAP followed by hydrogenolysis of the resulting (2′-O-phenoxythiocarbonyl) phenyl thionocarbonate esters (6) with tributylstannane/AIBN, and deprotection, gave 2′-deoxy-β-D-threo-pentofuranosyl nucleosides (7). Formation of a by-product bis(nucleosid-2′-yl)thionocarbonate dimer (8) was detected in the uracil nucleoside reaction sequence. Its subsequent reduction provides one explanation for "reversion to starting alcohol" in Barton-type deoxygenation reactions. Only the guanine 2′-deoxynucleoside analogue (7b) had (weak) antiviral activity (against herpes simplex virus type 1).

scholarly journals C-5 Hydroxyethyl and Hydroxypropyl Acyclonucleosides as Substrates for Thymidine Kinase of Herpes Simplex Virus Type 1 (HSV-1 TK): Syntheses and Biological Evaluation

Molecules ◽  
2013 ◽  
Vol 18 (5) ◽  
pp. 5104-5124 ◽  
Author(s):  
Andrijana Meščić ◽  
Svjetlana Krištafor ◽  
Ivana Novaković ◽  
Amar Osmanović ◽  
Ursina Müller ◽  
...  
Keyword(s):  
Herpes Simplex Virus ◽  
Herpes Simplex ◽  
Thymidine Kinase ◽  
Virus Type ◽  
Herpes Simplex Virus Type ◽  
Biological Evaluation ◽  
Simplex Virus ◽  
Hsv 1

scholarly journals Inhibition of Herpes Simplex Virus Types 1 and 2 In Vitro Infection by Sulfated Derivatives of Escherichia coli K5 Polysaccharide

2008 ◽  
Vol 52 (9) ◽  
pp. 3078-3084 ◽  
Author(s):  
Debora Pinna ◽  
Pasqua Oreste ◽  
Tiziana Coradin ◽  
Anna Kajaste-Rudnitski ◽  
Silvia Ghezzi ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Herpes Simplex Virus ◽  
Herpes Simplex ◽  
Simplex Virus ◽  
Derivatives Of ◽  
Hiv 1 ◽  
K5 Polysaccharide ◽  
Hsv 1

ABSTRACT Herpes simplex virus type 1 (HSV-1) and HSV-2 are neurotropic viruses and common human pathogens causing major public health problems such as genital herpes, a sexually transmitted disease also correlated with increased transmission and replication of human immunodeficiency virus type 1 (HIV-1). Therefore, compounds capable of blocking HIV-1, HSV-1, and HSV-2 transmission represent candidate microbicides with a potential added value over that of molecules acting selectively against either infection. We report here that sulfated derivatives of the Escherichia coli K5 polysaccharide, structurally highly similar to heparin and previously shown to inhibit HIV-1 entry and replication in vitro, also exert suppressive activities against both HSV-1 and HSV-2 infections. In particular, the N,O-sulfated [K5-N,OS(H)] and O-sulfated epimerized [Epi-K5-OS(H)] forms inhibited the infection of Vero cells by HSV-1 and -2, with 50% inhibitory concentrations (IC50) between 3 ± 0.05 and 48 ± 27 nM, and were not toxic to the cells at concentrations as high as 5 μM. These compounds impaired the early steps of HSV-1 and HSV-2 virion attachment and entry into host cells and reduced the cell-to-cell spread of HSV-2. Since K5-N,OS(H) and Epi-K5-OS(H) also inhibit HIV-1 infection, they may represent valid candidates for development as topical microbicides preventing sexual transmission of HIV-1, HSV-1, and HSV-2.

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