Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives

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Title:Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 9, pp. 1393-1406
Uncontrolled Keywords:Thiols, Purines, Alkylation, Thiones, Acyclic nucleoside and nucleotide analogs, Hydrolysis

Abstract

Alkylation of 6-amino-7<i>H</i>-purin-8(9<i>H</i>)-thione (8-sulfanyladenine, <strong>1</strong>) with one equivalent of (<i>R</i>)-[(trityloxy)methyl]oxirane gave its <i>S</i>-alkyl derivative <strong>2</strong>, which was converted to the 6-amino-7<i>H</i>-purin-8(9<i>H</i>)-one (<strong>3</strong>), while alkylation of <strong>1</strong> with two equivalents of (<i>S</i>)-[(trityloxy)methyl]oxirane afforded a mixture of <i>N</i><sup>3</sup>,<i>S</i>-dialkylated product <strong>4a</strong>, <i>N</i><sup>9</sup>-monoalkyl and <i>N</i><sup>7</sup>,<i>N</i><sup>9</sup>-dialkyl derivatives of 6-amino-7<i>H</i>-purin-8(9<i>H</i>)-one, <strong>5a</strong> and <strong>6a</strong>, respectively. This approach can be used for rapid and easy transformation of 8-[(2-hydroxyalkyl)sulfanyl]adenines to the derivatives of 6-amino-7<i>H</i>-purin-8(9<i>H</i>)-one (8-hydroxyadenine) using NaH or Cs<sub>2</sub>CO<sub>3</sub> in DMF. The course of the S→O transformation strictly depends on the character of the starting compounds and on the reaction conditions. <i>N</i><sup>9</sup>-Alkyl-8-[(2-hydroxyalkyl)sulfanyl]adenines <strong>10</strong>, <strong>12</strong>, <strong>14</strong> and <strong>17</strong> were rapidly converted to the corresponding 6-amino-7<i>H</i>-purin-8(9<i>H</i>)-one derivatives <strong>11</strong>, <strong>13</strong>, <strong>11</strong> and <strong>18</strong>, respectively. <i>N</i><sup>9</sup>-Unsubstituted <strong>2</strong> reacts slowly, and <i>N</i><sup>3</sup>-alkyl derivative <strong>4a</strong> is stable under the same reaction conditions. The described transformation does not occur when the hydroxy group in 8-[(2-hydroxyalkyl)sulfanyl]adenine derivative <strong>15</strong> is protected. The reaction using NaH proceeds more rapidly than that using Cs<sub>2</sub>CO<sub>3</sub>. <p>

Title:Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Uncontrolled Keywords:Thiols, Purines, Alkylation, Thiones, Acyclic nucleoside and nucleotide analogs, Hydrolysis
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:9
Page Range:pp. 1393-1406
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011393UNSPECIFIED
ID Code:1865
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Janeba, Zlatko; Holý, Antonín; Masojídková, Milena (2001) Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives. Collection of Czechoslovak Chemical Communications, 66 (9). pp. 1393-1406. ISSN 0010-0765

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