Synthesis and biological evaluation of some 4-substituted 1-[1-(4-hydroxybutyl)-1,2,3-triazol-(4 &5)-ylmethyl]-1H-pyrazolo- 13,4-dipyrimidines.
The synthesis of 1-[1-(4-hydroxybutyl)-1,2,3-triazol-(4 and 5)-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines 11a,b, 12a,b and 13-17 as carboacyclic nucleosides is described. The compounds 8a,b were condensed, separately, with compound 7 via 1,3-dipolar cycloaddition reaction to afford, after separation and deprotection. 1,4-regioisomers 11a,b and 1,5-regioisomers 12a,b. The deprotected carboacyclic nucleosides 11a served as precursor for the preparation of 4-amino 13. 4-methylamino 14, 4-benzylamino 15, 4-methoxy 16 and 4-hydroxy 17 analogues. All deprotected carboacyclic nucleosides were evaluated for their inhibitory effects against the replication of HIV-1(III), HIV-2(ROD), various DNA viruses, a variety of tumor-cell lines and tuberculosis. No marked biological activity was found.
Moukha-Hafiq
O
O
Laboratoire de Chimie Bio-Organique, Faculté des Sciences, Agadir, Morocco.
Taha
M L
ML
Lazrek
H B
HB
Vasseur
J J
JJ
Pannecouque
C
C
Witvrouw
M
M
De Clercq
E
E
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002460:Cell Line; D005347:Fibroblasts / Q000378:metabolism; D006678:HIV / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D013696:Temperature; D014407:Tumor Cells, Cultured
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D009705:Nucleosides; D011743:Pyrimidines