A facile synthesis and anti-avian influenza virus (H5N1) screening of some novel pyrazolopyrimidine nucleoside derivatives.
Treatment of 5-amino-1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazole-4-carbonitrile (1) with formic acid afforded pyrazolo[3,4-d]pyrimidin-4-one derivative 2. The sodium salt of the latter compound (generated in situ) was treated with some alkyl halides to afford the corresponding N-substituted compounds 3-7. The siloxy derivative 8 (generated also in situ from 2) was ribosylated and glycosylated to yield compounds 9 and 11, respectively. Deprotection of compounds 9 and 11 in methanolic ammonia produced the free nucleosides 10 and 12, respectively. Moreover, the prepared compounds were tested for antiviral activity against H5N1 virus [A/chicken/Egypt/1/2006] and some of them revealed moderate results compared with the other tested compounds.
Photochemistry Department, National Research Center, Elbehos Street, Dokki, Cairo, Egypt. aymnelzeny@yahoo.com
Aymn E
AE
Rashad
Ahmed H
AH
Shamroukh
Randa E
RE
Abdel-Megeid
Ahmed
A
Mostafa
Mohamed A
MA
Ali
Klaus
K
Banert
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D004285:Dogs; D005561:Formates / Q000737:chemistry; D053124:Influenza A Virus, H5N1 Subtype / Q000187:drug effects*; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000737:chemistry*
D000998:Antiviral Agents; D005561:Formates; D011720:Pyrazoles; D011741:Pyrimidine Nucleosides; C030544:formic acid