Synthesis and biological evaluation of some alpha-[6-(1'-carbamoylalkylthio)-1 H-pyrazolo[3,4-D]pyrimidin-4-yl]thioalkylcarboxamide acyclonucleosides.
The reaction of 1H-pyrazolo[3,4-d]pyrimidin-4,6-dithione 11 with compounds 12a-c produces ethyl alpha-[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 N(1)-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.
Moukha-Chafiq
Omar
O
Faculté des Sciences, Laboratoire de Chimie Bio-Organique Appliquée, Agadir, Morocco. moukhachafiqe@sri.org
Taha
Mohamed Labd
ML
Mouna
Abdelmalek
A
Lazrek
Hassan Bihi
HB
Vasseur
Jean-Jacques
JJ
De Clercq
Erik
E
D003587:Cytomegalovirus / Q000254:growth & development*; D014645:Herpesvirus 3, Human / Q000254:growth & development*; D006801:Humans; D009169:Mycobacterium tuberculosis / Q000254:growth & development*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D014779:Virus Replication / Q000187:drug effects*
D009705:Nucleosides