Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives.
2-(3-Hydroxy-5,5-dimethylcyclohexylidene)malononitrile 5 undergoes an azo coupling reaction with aryldiazonium salts to afford 3-amino-2-aryl-6,6-dimethyl-8-oxo-2,6,7,8-tetrahydrocinnoline-4-carbonitriles 7. Upon reflux in acetic acid, these compounds were acetylated to give the cinnoline derivatives 9. The pyrazolones 10a, b react with 3-furfurylidene- and 3-thienylidene-malononitrile derivatives 11a, b to afford the pyrano[2,3-c]pyrazole derivatives 13a-d. These newly synthesized compounds show generally a moderate molluscicidal activity to Biomphalaria alexandrina snails.
Abdelrazek
Fathy M
FM
Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt. prof_fmrazek@yahoo.com
Metz
Peter
P
Metwally
Nadia H
NH
El-Mahrouky
Sherif F
SF
D000818:Animals; D001700:Biomphalaria / Q000187:drug effects / Q000254:growth & development; D004305:Dose-Response Relationship, Drug; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000633:toxicity; D015394:Molecular Structure; D008975:Molluscacides / Q000138:chemical synthesis* / Q000633:toxicity; D011714:Pyrans / Q000138:chemical synthesis* / Q000633:toxicity; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000633:toxicity; D013329:Structure-Activity Relationship; D018675:Toxicity Tests / Q000379:methods
D006574:Heterocyclic Compounds, 2-Ring; D008975:Molluscacides; D011714:Pyrans; D011720:Pyrazoles; C476282:cinnoline