Synthesis of AZT analogues: 7-(3-azido-2hydroxypropyl)-, 7-(3-amino-2-hydroxypropyl)-, 7-(3-triazolyl-2-hydroxypropyl) theophyllines

ESH El Ashry, A Abdel-Rahman, N Rashed…

Index: El Ashry, El Sayed; Abdel-Rahman, Adel; Rashed, Nagwa; Awad, Laila; Rasheed, Hanaa Nucleosides, Nucleotides and Nucleic Acids, 2006 , vol. 25, # 3 p. 299 - 305

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Citation Number: 9

Abstract

Nucleophilic displacement of the tosyloxy group in 7-(2-hydroxy-3-p- toluenesulfonyloxypropyl) theophylline (1) with azide anion afforded 7-(3-azido-2- hydroxypropyl) theophylline (2). Reduction of the 3-azido group in 2 with Ph3P/Py/NH4OH afforded the 3-amino derivative 4, alternatively obtained by regioselective amination of 7-(2, 3-epoxypropyl) theophylline (3). Selective acetylation of 4 gave the N-acetyl derivative 5. 1 ...