Synthesis, and Antitumor Activity of Some N1-(Coumarin-7-yl) Amidrazones and Related Congeners

• Main Authors: Mohammad S. Mustafa, Mustafa M. El-Abadelah, Malek A. Zihlif, Randa G. Naffa, Mohammad S. Mubarak
• Format: Article
• Language: English
• Published: MDPI AG 2011-05-01
• Series: Molecules
• Subjects: 7-aminocoumarins; N-(coumarin-7-yl)hydrazonoyl chloride; 1-piperazinyl amidrazones; nitrileimine; antitumor activity
• Online Access: http://www.mdpi.com/1420-3049/16/5/4305/
• ISSN: 1420-3049

A series of new N1-(coumarin-7-yl)amidrazones incorporating N-piperazines and related congeners were synthesized by reacting the hydrazonoyl chloride derived from 7-amino-4-methylcoumarin with the appropriate piperazines. The chemical structures of the newly prepared compounds were supported by elemental analyses, 1H-NMR, 13C-NMR, and ESI-HRMS spectral data. The antitumor activity of the newly synthesized compounds was evaluated. Among all the compounds tested, 7-{2-[1-(4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)piperazin-1-yl)-2-oxopropylidene]hydrazinyl}-4-methyl-2H-chromen-2-one (3n) was the most potent against MCF-7 and K562 cells, with IC50 values of 20.2 and 9.3 μM, respectively.