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. 2011 May 24;16(5):4305-17.
doi: 10.3390/molecules16054305.

Synthesis, and antitumor activity of some N1-(coumarin-7-yl) amidrazones and related congeners

Mohammad S Mustafa  1 , Mustafa M El-Abadelah, Malek A Zihlif, Randa G Naffa, Mohammad S Mubarak
Affiliations

Synthesis, and antitumor activity of some N1-(coumarin-7-yl) amidrazones and related congeners

Mohammad S Mustafa et al. Molecules. .

Abstract

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.

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Figures

Scheme 1
Scheme 1
Synthesis of N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-oxopropanehydrazonoyl chloride (2).
Scheme 2
Scheme 2
Synthesis of 4-methyl-7-{2-[2-oxo-1-(substituted N-hexahydroazinyl)propylidene]-hydrazinyl}-2H-chromen-2-ones 3a-n.
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