Synthesis and Biological Evaluation of Some α-[6-(1'-Carbamoylalkylthio)-1 H-Pyrazolo[3,4-D]Pyrimidin-4-yl]Thioalkylcarboxamide Acyclonucleosides

Author: Moukha-Chafiq Omar   Taha Mohamed Labd   Mouna Abdelmalek   Lazrek Hassan Bihi   Vasseur Jean-Jacques   De Clercq Erik  

Publisher: Taylor & Francis Ltd

ISSN: 1525-7770

Source: Nucleosides, Nucleotides & Nucleic Acids, Vol.26, Iss.4, 2007-04, pp. : 335-345

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Abstract

The reaction of 1H-pyrazolo[3,4-d]pyrimidin-4,6-dithione 11 with compounds 12a-c produces ethyl α-[6-(1'-carboethoxyalkylthio)-1 H-pyrazolo[3,4-d]pyrimidin-4-yl]thioalkylates 13a-c, respectively. These heterocycles were alkylated, separately, with alkylating agents 14, 15, and 16 to afford, predominately, the N1-acyclic nucleosides (17-19)a-c, which were deprotected to give the desired products (20-22)a-c. All synthetic compounds were characterized on the basis of their physical and spectroscopic properties. The acyclic nucleosides (20-22)a-c were evaluated for their inhibitory effects against the replication of varicella-zoster virus, human cytomegalovirus and M. tuberculosis. No marked biological activity was found.

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