Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine

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Title:Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 11, pp. 1698-1712
Uncontrolled Keywords:Purines, Alkylation, Nucleosides, Mitsunobu reaction, Cyclization, Anhydro derivatives, Nucleotides, Acyclic nucleoside and nucleotide analogues

Abstract

Reaction of 8-bromoadenine derivatives <strong>1</strong> with thiourea in ethanol or butanol was used for the synthesis of the corresponding <i>N</i><sup>9</sup>-substituted 6-amino-7<i>H</i>-purine-8(9<i>H</i>)-thiones <strong>2</strong>. 8-(Methylsulfanyl)adenine derivatives <strong>3</strong> were prepared by reaction of thiones <strong>2</strong> with iodomethane in 1 M sodium methoxide or in aqueous 1.5 M potassium hydroxide. Alkylation of 6-amino-7<i>H</i>-purine-8(9<i>H</i>)-thione (<strong>2a</strong>) proceeds preferentially on the sulfur atom. Under similar conditions, alkylation of 8-(methylsulfanyl)adenine (<strong>3a</strong>) with diverse alkylation agents afforded <i>N</i><sup>9</sup>-substituted adenine derivatives <strong>3</strong> and <strong>6</strong>, and <i>N</i><sup>3</sup>-substituted adenine derivatives <strong>5</strong> and <strong>7</strong>. 8,3'-<i>S</i>-Anhydro derivatives <strong>9</strong> were prepared in good yields by cyclization of 6-amino-7<i>H</i>-purine-8(9<i>H</i>)-thiones <strong>2d</strong> and <strong>2f</strong> under the Mitsunobu reaction conditions. <p>

Title:Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Uncontrolled Keywords:Purines, Alkylation, Nucleosides, Mitsunobu reaction, Cyclization, Anhydro derivatives, Nucleotides, Acyclic nucleoside and nucleotide analogues
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:65
Number:11
Page Range:pp. 1698-1712
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001698UNSPECIFIED
ID Code:1751
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Janeba, Zlatko; Holý, Antonín; Masojídková, Milena (2000) Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine. Collection of Czechoslovak Chemical Communications, 65 (11). pp. 1698-1712. ISSN 0010-0765

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