Synthesis and Molluscicidal Activity of New Cinnoline and Pyrano [2,3‐c]pyrazole Derivatives

Abstract

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.

Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions

“…Polyfunctionalized 4H-pyran structural motifs occur in a variety of natural products (14,15) and also constitute biologically interesting compounds (11Á13, 16, 17, 18Á 22). Pyranopyrazoles prevalently hold a position of prominence attributing to their biological activities which include insecticidal (23) anti-inflammatory (24), molluscicidal (25,26), besides being identified as a screening kit for Chk1 kinase inhibitor (27).…”

Ag/Tio2 Nano Thin Films Catalyzed Efficient Synthesis of 6-Amino-4-Aryl-3-Methyl-1,4-Dihydropyrano[2,3-C] Pyrazole-5-Carbonitriles At Green Conditions

“…Dihydropyrano [2,3-c]pyrazoles, are one of the most important pyrazole compounds and they have received considerable attention owing to their biological activity and they have been utilize as a template for medicinal chemistry. They exhibited many biological activities like antimicrobial 26 , insecticidal 27 , and anti-inflammatory 28 . Moreover, dihydropyrano [2,3-c]pyrazoles exhibit molluscicidal activity 29 , and has been identified as a screening kit for Chk1 kinase inhibitor 30 .…”

A Rapid, Convient and Diversified-Multicomponent Synthesis and Characterization of Pyrano[2,3-<i>b</i>]Indoles

“…Compounds containing this moiety have many pharmacological properties and play important roles in biochemical processes. They are reported to possess a multiplicity of pharmacological properties including anticancer 7 , antimicrobial 8 , anti-inflammatory 9 , insecticidal, and molluscicidal activities 10,11 . They are also potential inhibitors of human Chk1 kinase 12 .…”