Abstract
The considerable biological and medicinal activities of purine nucleoside derivatives have simulated the recent interest in the synthesis of some new purine nucleosides. The present work described the reaction of inosine (1) with triphenylphosphine which led to the formation of 5-chloro-5-deoxy inosine (2), which on reaction with methylamine and morphorine afforded the compounds (3) and (4) respectively. The benzoylation of inosine (1) with benzoylchloride led to the formation of 1-benzoyl inosine (5) followed by reaction with sodium hydroxide affording compound (6). While the treatement of inosine (1) with dichlorodimethylsilane gave the compound (7), which on reaction with ethylacrylate gave 1-etheoxycarbonylethyl-3, 5-O-(di-methylsilanediyl) ether inosine (8). Treatment of inosine (1) with methane sulfonylchloride led to the formation 3,5-dimethanesulfonylinosine (9) which reacted with bormine to give 8-bromo-3,5- dimethanesulfonylinosine (10) was allowed to react with thiourea to give 8-mercapto -3,5-dimehanesulfonylinosine (11). The biological activities of the prepared compounds were also described.
Current Organic Chemistry
Title: Synthesis of Some Purine Nucleoside Derivatives with Expected Biological Activity
Volume: 13 Issue: 18
Author(s): A. F. El-Farargy and Amira A. Ghoneim
Affiliation:
Abstract: The considerable biological and medicinal activities of purine nucleoside derivatives have simulated the recent interest in the synthesis of some new purine nucleosides. The present work described the reaction of inosine (1) with triphenylphosphine which led to the formation of 5-chloro-5-deoxy inosine (2), which on reaction with methylamine and morphorine afforded the compounds (3) and (4) respectively. The benzoylation of inosine (1) with benzoylchloride led to the formation of 1-benzoyl inosine (5) followed by reaction with sodium hydroxide affording compound (6). While the treatement of inosine (1) with dichlorodimethylsilane gave the compound (7), which on reaction with ethylacrylate gave 1-etheoxycarbonylethyl-3, 5-O-(di-methylsilanediyl) ether inosine (8). Treatment of inosine (1) with methane sulfonylchloride led to the formation 3,5-dimethanesulfonylinosine (9) which reacted with bormine to give 8-bromo-3,5- dimethanesulfonylinosine (10) was allowed to react with thiourea to give 8-mercapto -3,5-dimehanesulfonylinosine (11). The biological activities of the prepared compounds were also described.
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Cite this article as:
El-Farargy F. A. and Ghoneim A. Amira, Synthesis of Some Purine Nucleoside Derivatives with Expected Biological Activity, Current Organic Chemistry 2009; 13 (18) . https://dx.doi.org/10.2174/138527209789630488
DOI https://dx.doi.org/10.2174/138527209789630488 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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