Synthesis of new pyrrole and pyrrolo[2,3-d]pyrimidine derivatives of potential antioxidant activity

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Title:Synthesis of new pyrrole and pyrrolo[2,3-d]pyrimidine derivatives of potential antioxidant activity
Creators:
El-Bayouki, Khairy Abdelhameed Mohsen
Basyouni, Wahid Mohmoud
Mostafa, Eslam Attya
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 75, 8, pp. 813-834
Uncontrolled Keywords:Quaternization, Triazole, Pyrrole, Tetrazole, Pyrrolo[2,3-<i>d</i>]pyrimidine, Antioxidant activity

Abstract

New 2-amino-3-cyanopyrrole derivatives were prepared and converted to 7-deazapurines. 7-Deazaadenine <b>6</b> was synthesized by different methods and alkylated with alkyl iodides to afford the quaternized 3-alkylpyrrolopyrimidinium iodide salts <b>8</b>. The latter salts were dequaternized to <i>N</i>-alkylpyrrolo[2,3-<i>d</i>]pyrimidin-4-amines <b>12</b>. Compounds <b>12</b> were identical to the products obtained from reactions of 4-chloro-7-(4-fluorophenyl)-5-<i>p</i>-tolyl-7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidine <b>11</b> with methyl- or ethylamine in the presence of a catalyst. The thione <b>13</b> and its related 4-methylthio- and 4-ylcarbonothioate derivatives <b>14a</b>, <b>14b</b> were obtained. The triazolo- <b>17a</b>–<b>17e</b>, benzenesulfonamido- <b>19</b>, and tetrazolopyrrolopyrimidine <b>21</b> derivatives were synthesized. Several examples of the synthesized pyrrole- and pyrrolo[2,3-<i>d</i>]pyrimidine derivatives showed high to remarkable antioxidant scavenging activity as measured by their ability to scavenge the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical

Title:Synthesis of new pyrrole and pyrrolo[2,3-d]pyrimidine derivatives of potential antioxidant activity
Creators:
El-Bayouki, Khairy Abdelhameed Mohsen
Basyouni, Wahid Mohmoud
Mostafa, Eslam Attya
Uncontrolled Keywords:Quaternization, Triazole, Pyrrole, Tetrazole, Pyrrolo[2,3-<i>d</i>]pyrimidine, Antioxidant activity
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:75
Number:8
Page Range:pp. 813-834
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2009566UNSPECIFIED
ID Code:6193
Item Type:Article
Deposited On:11 Oct 2010 15:42
Last Modified:11 Oct 2010 13:43

Citation

El-Bayouki, Khairy Abdelhameed Mohsen; Basyouni, Wahid Mohmoud; Mostafa, Eslam Attya (2010) Synthesis of new pyrrole and pyrrolo[2,3-d]pyrimidine derivatives of potential antioxidant activity. Collection of Czechoslovak Chemical Communications, 75 (8). pp. 813-834.

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