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

ChemInform ◽  
2006 ◽  
Vol 37 (40) ◽  
Author(s):  
Michal Sala ◽  
Hubert Hrebabecky ◽  
Milena Masojidkova ◽  
Antonin Holy
Keyword(s):  
Carbocyclic Nucleosides ◽  
Conformationally Locked

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.

Conformationally Locked Carbocyclic Nucleosides: Synthesis of the 1-Methyl-6-oxabicyclo[3.1.0]hexane Scaffold

Synlett ◽  
2006 ◽  
Vol 2006 (14) ◽  
pp. 2215-2218
Author(s):  
Gérard Audran ◽  
Honoré Monti ◽  
Yoann Aubin
Keyword(s):  
Carbocyclic Nucleosides ◽  
Conformationally Locked

Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides

2005 ◽  
Vol 70 (1) ◽  
pp. 103-123 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Carbocyclic Nucleosides ◽  
Purine Derivatives ◽  
Purine Analogues ◽  
Derivatives Of ◽  
Conformationally Locked

(1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-Amino-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols (16aand17a) were prepared from 2-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2-methanol (10) in five easy steps. The amines16aand17awere used to construct 6-chloro-9H-purine20and21, 2-amino-6-chloro-9H-purine30and31, and 6-chloro-8-methyl-9H-purine analogues34and35. Ammonolysis of these compounds led to 6-amino-9H-purine22aand23a, 2,6-diamino-9H-purine32and33, and 6-amino-8-methyl-9H-purine derivatives of 5-oxatricyclo[4.2.1.03,7]nonane-3-methanol36and37. (1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-[6-(Dimethylamino)-9H-purin-9-yl]-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols (22band23b), and (1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-[6-(cyclopropylamino)-9H-purin-9-yl]-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols (22cand23c) were prepared by aminolysis of20and21.

Synthesis of conformationally locked carbocyclic nucleosides with norbornane as pseudosugar moiety

2011 ◽  
Author(s):  
Milan Dejmek ◽  
Hubert Hřebabecký ◽  
Michal Šála ◽  
Martin Dračínský ◽  
Radim Nencka
Keyword(s):  
Carbocyclic Nucleosides ◽  
Conformationally Locked

Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol

2006 ◽  
Vol 71 (6) ◽  
pp. 871-888 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Milena Masojídková ◽  
Martin Dračínský ◽  
Antonín Holý
Keyword(s):  
Liquid Ammonia ◽  
Transfer Hydrogenation ◽  
Carbocyclic Nucleosides ◽  
Purine Analogues ◽  
Purine Derivative ◽  
Purine Analogue ◽  
Conformationally Locked

(1R*,2R*,3R*,4R*,5R*,6S*)-3-Amino-5-(benzyloxy)-6-(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (18) was prepared in seven easy steps from benzyl (1R*,2S*,3S*,4S*)-3-(benzyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate (10). Reaction of amine18with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded 1-[(1R*,2R*,3R*,4R*,5S*,6R*)-6-(benzyloxy)-3-hydroxy-5- (hydroxymethyl)bicyclo[2.2.1]heptan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (21) and after deprotection by transfer hydrogenation, free thymine analogue22. The thymine derivative21was converted to 2,3'-anhydronucleoside26. Treatment of the benzyl derivative18with sodium in liquid ammonia led to amine19, which was used as key intermediate for the construction of (1R*,2R*,3R*,4R*,5R*,6S*)-3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)-bicyclo[2.2.1]heptane-2,5-diol (28) and (1R*,2R*,3R*,4R*,5R*,6S*)-3-(2-amino-6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol (33). Ammonolysis of28led to 6-amino-9H-purine derivative29. 6-(Dimethylamino)-9H-purine analogue30and 6-(cyclopropylamino)-9H-purine analogues31and34were prepared by aminolysis of corresponding chloropurine derivatives.

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