Conformationally locked carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template with a fixed Southern conformation. Synthesis and antiviral activity

1997 ◽  
pp. 1073-1078 ◽  
Author(s):  
Abdallah Ezzitouni ◽  
Victor E. Marquez
Keyword(s):  
Antiviral Activity ◽  
Carbocyclic Nucleosides ◽  
Conformationally Locked

Synthesis and Antiviral Activity of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. Part 3: Adenosine and Uridine Analogues

1999 ◽  
Vol 18 (10) ◽  
pp. 2253-2263 ◽  
Author(s):  
M. Isabel Nieto ◽  
J. Manuel Blanco ◽  
Olga Caamaño ◽  
Franco Fernández ◽  
Xerardo Garcia-mera ◽  
...  
Keyword(s):  
Antiviral Activity ◽  
Carbocyclic Nucleosides ◽  
Cyclopentane Ring

Synthesis and antiviral activity of 2′‐deoxy‐6′‐substituted carbocyclic nucleosides

2021 ◽  
Author(s):  
Haitao Xue ◽  
Shuang Guo ◽  
Tianwen Hu ◽  
Daibao Wei ◽  
Yuanchao Xie ◽  
...  
Keyword(s):  
Antiviral Activity ◽  
Carbocyclic Nucleosides

scholarly journals Contrasting Behavior of Conformationally Locked Carbocyclic Nucleosides of Adenosine and Cytidine as Substrates for Deaminases

2009 ◽  
Vol 28 (5-7) ◽  
pp. 614-632 ◽  
Author(s):  
Victor E. Marquez ◽  
Gottfried K. Schroeder ◽  
Olaf R. Ludek ◽  
Maqbool A. Siddiqui ◽  
Abdallah Ezzitouni ◽  
...  
Keyword(s):  
Carbocyclic Nucleosides ◽  
Conformationally Locked

Synthesis of Novel Racemic Conformationally Locked Carbocyclic Nucleosides Derived from 7-Substituted Bicyclo[2.2.1]hept-5-ene-2,2-dimethanols

2006 ◽  
Vol 71 (5) ◽  
pp. 635-649 ◽  
Author(s):  
Michal Šála ◽  
Hubert Hřebabecký ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Trifluoroacetic Acid ◽  
Palladium Catalyst ◽  
Carbocyclic Nucleosides ◽  
Purine Derivative ◽  
Adenine Derivative ◽  
Conformationally Locked

(1R*,4R*,7S*)-7-Aminobicyclo[2.2.1]hept-5-ene-2,2-dimethanol (15) was prepared in four easy steps from bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (10). Reaction of amine 15 with ethyl N-((E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives 17a. The amine 15 was used to construct 6-chloro-9H-purine derivative 19a, 2-amino-6-chloro-9H-purine derivative 22a. Ammonolysis of 19a led to the adenine derivative 20a. Treatment of 22a with trifluoroacetic acid afforded guanine nucleoside 23a. (1R*,4R*,7S*)-7-[6-(Cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (21a) and (1R*,4R*,7S*)-7-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]bicyclo[2.2.1]hept-5-ene-2,2-dimethanol (24a) were prepared by aminolysis of 19a and 22a. Saturated nucleosides 17b, 20b, 21b, 23b, 24b were obtained by hydrogenation on palladium catalyst.

SYNTHESIS AND EVALUATION OF ANTIVIRAL ACTIVITY OF HIGHER HOMOLOGUES OF XYLO-CARBOCYCLIC NUCLEOSIDES

2001 ◽  
Vol 20 (4-7) ◽  
pp. 1137-1139 ◽  
Author(s):  
O. Caamaño ◽  
M. J. Figueira ◽  
F. Fernández ◽  
M. D. García ◽  
M. I. Nieto ◽  
...  
Keyword(s):  
Antiviral Activity ◽  
Carbocyclic Nucleosides

scholarly journals Syntheses of Isoxazoline-Carbocyclic Nucleosides and Their Antiviral Evaluation: A Standard Protocol

2014 ◽  
Vol 2014 ◽  
pp. 1-12 ◽  
Author(s):  
Paolo Quadrelli ◽  
Naiara Vazquez Martinez ◽  
Roberto Scrocchi ◽  
Antonino Corsaro ◽  
Venerando Pistarà
Keyword(s):  
Antiviral Activity ◽  
Rna Viruses ◽  
Carbocyclic Nucleosides ◽  
Standard Protocol ◽  
Dna And Rna ◽  
Biological Tests ◽  
Key Steps ◽  
The Way

The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests.

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