A facile synthesis and anti-avian influenza virus (H5N1) screening of some novel pyrazolopyrimidine nucleoside derivatives

Article abstract of DOI:10.1080/15257770.2010.529480

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. Copyright

Full text of DOI:10.1080/15257770.2010.529480

Antiviral and Antischistosomal Evaluation of Newly Synthesized
Thioglycosides and their Acyclic Analogues
Aladdin M. Sroura,*, Abd El-Hamid A. Ismailb, Salah M. El-Kosyb,
and Ibrahim F. Zeidb
a
Therapeutical Chemistry Department, National Research Centre, Cairo, Egypt.
E-mail: dr_aladdinms@yahoo.com
Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koom, Egypt
b
* Author for correspondence and reprint requests
Z. Naturforsch. 64c, 483–489 (2009); received January 30/March 18, 2009
The pyrimidine thione derivatives 2a– d were prepared by the reaction of thiourea, ethyl
cyanoacetate and several aromatic aldehydes. The acyclic thioglycosides 4a–7d were pre-
pared by the reaction of the synthesized pyrimidine thiones 2a– d with different alkyl hali-
des, whereas the reaction of 2a– d with 2,3,4,6-tetra-O-acetyl-α- -glucopyranosyl bromide
D
afforded the cyclic thioglycosides 8a– d whose deprotection afforded 9a– d. The obtained
compounds were tested for their antischistosomal and antiviral activity against hepatitis B
virus (HBV). Compounds 5a, 5d, 7a showed high activity against HBV using the MTT assay;
moreover compounds 5c, 6d, 7a, 9a, 9c exhibited high activity as antischistosomal agents.
Key words: Pyrimidine Thione, Thioglycosides, Antischistosomiasis