Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs

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Title:Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 3, pp. 517-532
Uncontrolled Keywords:Purines, Alkylation, Acyclic nucleotide analogues, Nucleosides, Amines, <i>N</i>-Cyclonucleosides, Antivirals

Abstract

8-Aminoadenine derivatives <strong>2</strong> were obtained from 8-bromoadenines <strong>1</strong> in one-pot reaction <i>via</i> 8-azidoadenines. Reaction of 8-bromoadenines <strong>1</strong> with methylamine or dimethylamine in ethanol afforded the corresponding <i>N</i><sup>9</sup>-substituted 8-(methylamino)adenines <strong>3</strong> and 8-(dimethylamino)adenines <strong>4</strong>. Alkylation of 8-aminoadenine (<strong>2a</strong>) with diverse alkylation agents afforded <i>N</i><sup>9</sup>-substituted 8-aminoadenine derivatives <strong>2</strong>, and alkylation of 8-(dimethylamino)adenine (<strong>4a</strong>) gave mixtures of the corresponding <i>N</i><sup>9</sup>-substituted 8-(dimethylamino)adenines <strong>4</strong> and their <i>N</i><sup>3</sup>-substituted regioisomers <strong>5</strong>. 8,3'-<i>N</i>-Anhydro derivatives <strong>7</strong> were prepared by tosylation of (<i>S</i>)-8-bromo-9-{2-[(diisopropoxyphosphoryl)- methoxy]-3-hydroxypropyl}adenine (<strong>1c</strong>) followed by treatment with methanolic ammonia or methylamine solution. <p>

Title:Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Uncontrolled Keywords:Purines, Alkylation, Acyclic nucleotide analogues, Nucleosides, Amines, <i>N</i>-Cyclonucleosides, Antivirals
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:66
Number:3
Page Range:pp. 517-532
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20010517UNSPECIFIED
ID Code:1807
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Janeba, Zlatko; Holý, Antonín; Masojídková, Milena (2001) Synthesis of 8-Amino- and N-Substituted 8-Aminoadenine Derivatives of Acyclic Nucleoside and Nucleotide Analogs. Collection of Czechoslovak Chemical Communications, 66 (3). pp. 517-532. ISSN 0010-0765

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