Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses

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Title:Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses
Creators:
Hřebabecký, Hubert
Dračínský, Martin
Palma, Armando M. De
Neyts, Johan
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 74, 3, pp. 469-485
Uncontrolled Keywords:<i>Coxsackie</i> virus, Purines, Nucleosides, Amines, 9<i>H</i>-Purine-6-thiol, 5-Methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione, Thymine, Antivirals, 6-(Cyclopropylamino)purine, Adenine, Carbocyclic nucleosides, 6-(Dimethylamino)purine

Abstract

(1<i>R*</i>,2<i>R*</i>,3<i>R*</i>,4<i>S*</i>)-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dimethanol (<b>10</b>) and (1<i>R*</i>,2<i>R*</i>,3<i>R*</i>,4<i>S*</i>)-bicyclo[2.2.2]oct-5-ene-2,3-dimethanol (<b>14</b>), which were prepared by the Diels–Alder reaction and subsequent reduction with lithium aluminium hydride, were treated with benzyl azidoformate to give benzyl <i>N</i>-[(1<i>R*</i>,2<i>R*</i>,3<i>S*</i>,6<i>S*</i>,7<i>S*</i>,9<i>S*</i>)-9-(hydroxymethyl)-4,8-dioxatricyclo[4.2.1.0<sup>3,7</sup>]nonan-2-yl]carbamate (<b>11</b>) and benzyl <i>N</i>-[(1<i>R*</i>,2<i>R*</i>,3<i>R*</i>,6<i>R*</i>,7<i>S*</i>,10<i>S*</i>)-10-(hydroxymethyl)-4-oxatricyclo[4.3.1.0<sup>3,7</sup>]decan-2-yl]carbamate (<b>15</b>). Hydrogenolysis of carbamates <b>11</b> or <b>15</b> afforded (1<i>R*</i>,2<i>R*</i>,3<i>S*</i>,6<i>S*</i>,7<i>S*</i>,9<i>S*</i>)-2-amino-4,8-dioxatricyclo[4.2.1.0<sup>3,7</sup>]nonane-9-methanol (<b>12</b>) or (1<i>R*</i>,2<i>R*</i>,3<i>R*</i>,6<i>R*</i>,7<i>S*</i>,10<i>S*</i>)-2-amino-4-oxatricyclo[4.3.1.0<sup>3,7</sup>]decane-10-methanol (<b>16</b>). The amines <b>12</b> and <b>16</b> were transformed to thymine and purine nucleoside analogues. The target compounds were tested for the activity against <i>Coxsackie</i> virus.

Title:Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses
Creators:
Hřebabecký, Hubert
Dračínský, Martin
Palma, Armando M. De
Neyts, Johan
Holý, Antonín
Uncontrolled Keywords:<i>Coxsackie</i> virus, Purines, Nucleosides, Amines, 9<i>H</i>-Purine-6-thiol, 5-Methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione, Thymine, Antivirals, 6-(Cyclopropylamino)purine, Adenine, Carbocyclic nucleosides, 6-(Dimethylamino)purine
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:74
Number:3
Page Range:pp. 469-485
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2008193UNSPECIFIED
ID Code:4164
Item Type:Article
Deposited On:27 Mar 2009 11:33
Last Modified:27 Mar 2009 10:34

Citation

Hřebabecký, Hubert; Dračínský, Martin; Palma, Armando M. De; Neyts, Johan; Holý, Antonín (2009) Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses. Collection of Czechoslovak Chemical Communications, 74 (3). pp. 469-485. ISSN 0010-0765

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