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 Novel Conformationally Locked Carbocyclic Nucleosides Derived from 5,5- and 6,6-Bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol

2005 ◽  
Vol 70 (4) ◽  
pp. 519-538 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Double Bond ◽  
Chromatographic Separation ◽  
Carbocyclic Nucleosides ◽  
Purine Derivatives ◽  
Purine Analogues ◽  
Conformationally Locked

(1R*,2R*,3R*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (13) was prepared from (bicyclo[2.2.1]hept-5-ene-2,2-diyl)dimethyl dibenzoate (7) viacis-diol8, cyclic sulfate10, and azide12. (1R*,2R*,3S*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]-heptan-2-ol (18) and (1R*,2S*,3S*,4S*)-3-amino-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (19) were obtained by addition of chromyl azide to double bond of7, chromatographic separation, debenzoylation and hydrogenation of resulting azides14and16. The amines13,18, and19were used to build (1R*,2R*,3R*,4S*)- (21a), (1R*,2R*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21b), and (1R*,2S*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21c), respectively. Ammonolysis of these compounds led to 6-amino-9H-purine derivatives22a-22c. 6-(Dimethylamino)-9H-purine analogues23a-23cand 6-(cyclopropylamino)-9H-purine analogues24a-24cwere prepared by aminolysis of21a-21c. Reaction of amines13,18, and19with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives28a-28c.

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.

Heterocyclic derivatives of purines. 5. Nucleophilic substitution in series of imidazo[1,2-f]purine derivatives

1984 ◽  
Vol 20 (3) ◽  
pp. 330-334
Author(s):  
S. N. Garmash ◽  
B. A. Priimenko ◽  
N. A. Klyuev ◽  
N. I. Romanenko ◽  
A. K. Sheinkman
Keyword(s):  
Nucleophilic Substitution ◽  
Purine Derivatives ◽  
Heterocyclic Derivatives ◽  
In Series ◽  
Derivatives Of

Purine analogues as amplifiers of phleomycin. III. Some 2-alkylthio derivatives of imidazole, benzimidazole, benzoxazole and benzothiazole

1978 ◽  
Vol 31 (2) ◽  
pp. 447 ◽  
Author(s):  
DJ Brown ◽  
WC Dunlap ◽  
GW Grigg ◽  
L Danckwerts
Keyword(s):  
Escherichia Coli ◽  
Maximal Activity ◽  
Purine Analogues ◽  
Derivatives Of

Some 2-methylthio and 2-carbamoylalkylthio derivatives of 1-methylimidazole, benzimidazole, benzoxazole, benzothiazole and 6-dimethylaminobenzothiazole have been synthesized by alkylation of the corresponding thiones. Their in vitro activities, as amplifiers of phleomycin against Escherichia coli, varied from slight to high but none was outstanding. 2-(Benzothiazol-2'-ylthio)acetamide (2j)showed maximal activity at c. 0.04 mM with progressive decreases at both higher and lower concentrations.

Naphthalene derivatives of a conformationally locked GFP chromophore with large stokes shifts

2019 ◽  
Vol 60 (34) ◽  
pp. 150963 ◽  
Author(s):  
Nadezhda S. Baleeva ◽  
Anastasia V. Khavroshechkina ◽  
Elvira R. Zaitseva ◽  
Ivan N. Myasnyanko ◽  
Marina B. Zagudaylova ◽  
...  
Keyword(s):  
Naphthalene Derivatives ◽  
Gfp Chromophore ◽  
Derivatives Of ◽  
Stokes Shifts ◽  
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

Red-Shifted Fluorescent Aminated Derivatives of a Conformationally Locked GFP Chromophore

2014 ◽  
Vol 20 (41) ◽  
pp. 13234-13241 ◽  
Author(s):  
Mikhail S. Baranov ◽  
Kyril M. Solntsev ◽  
Nadezhda S. Baleeva ◽  
Alexander S. Mishin ◽  
Sergey A. Lukyanov ◽  
...  
Keyword(s):  
Gfp Chromophore ◽  
Derivatives Of ◽  
Conformationally Locked
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