Synthesis of AZT analogues: 7-(3-azido-2-hydroxypropyl)-, 7-(3-amino-2-hydroxypropyl)-,7-(3-triazolyl-2-hydroxypropyl)theophylline.
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. 1,3-Dipolar cycloaddition of the azide group in 2 with N1-propargyl thymine (6) afforded the regioisomeric triazole 7.
El Ashry
El Sayed H
el SH
Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt. eelashry60@hotmail.com
Abdel-Rahman
Adel
A
Rashed
Nagwa
N
Awad
Laila F
LF
Rasheed
Hanaa A
HA
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D012254:Ribavirin / Q000737:chemistry; D015215:Zidovudine / Q000031:analogs & derivatives*
D019380:Anti-HIV Agents; D012254:Ribavirin; D015215:Zidovudine