Synthesis and antiviral activity of new pyrazole and thiazole derivatives.
New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from alpha,beta-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel pyrazolothiazol-4(5H)-ones (13-16) or pyrazolothiazoles (17-24). The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC(50)) value of 7 microg/ml.
Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt. elsabbagh_59@yahoo.com
Osama I
OI
el-Sabbagh
Mohamed M
MM
Baraka
Samy M
SM
Ibrahim
Christophe
C
Pannecouque
Graciela
G
Andrei
Robert
R
Snoeck
Jan
J
Balzarini
Adel A
AA
Rashad
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D002522:Chlorocebus aethiops; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D014709:Vero Cells; D014780:Viruses / Q000187:drug effects
D000998:Antiviral Agents; D011720:Pyrazoles; D013844:Thiazoles; C031280:pyrazole