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  • Synthesis and antitumor activities of some new N1-(flavon-6-yl)amidrazone derivatives.

Synthesis and antitumor activities of some new N1-(flavon-6-yl)amidrazone derivatives.

Archiv der Pharmazie (2014-03-13)
Almeqdad Y Habashneh, Mustafa M El-Abadelah, Malek A Zihlif, Amer Imraish, Mutasem O Taha
ABSTRACT

A new series of N1-(flavon-6-yl)amidrazones were synthesized by reacting the hydrazonoyl chloride derived from 6-aminoflavone with the appropriate sec-cyclic amines. The antitumor activities of these compounds were evaluated on breast cancer (MCF-7) and leukemic (K562) cell lines. Among the compounds tested, the N-morpholine derivative was the most active against the MCF-7 and K562 cell lines, with IC50 values of 5.18 and 2.89 μM, respectively. Our docking studies showed that the N-morpholino derivative fits and blocks the oncogenic tyrosine kinases bcr/abl and epidermal growth factor receptor (EGFR) in a similar fashion to that of the potent anticancer agent imatinib.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Piperidine, SAJ first grade, ≥99.0%
Supelco
Morpholine, analytical standard
Sigma-Aldrich
Piperidine, ReagentPlus®, 99%
Sigma-Aldrich
Morpholine, ReagentPlus®, ≥99%
Sigma-Aldrich
6-Aminoflavone, 97%
Sigma-Aldrich
Piperidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Morpholine, purified by redistillation, ≥99.5%
Sigma-Aldrich
Morpholine, ACS reagent, ≥99.0%
Sigma-Aldrich
Thiomorpholine, 98%
Sigma-Aldrich
Piperidine, biotech. grade, ≥99.5%
Sigma-Aldrich
Piperazine, BioUltra, anhydrous, ≥99.0% (T)
Sigma-Aldrich
Morpholine, polymer-bound, 200-400 mesh, extent of labeling: 2.75-3.25 mmol/g loading, 1 % cross-linked
Sigma-Aldrich
1-Methylpiperazine, 99%
Sigma-Aldrich
3-Chloro-2,4-pentanedione, 97%
Sigma-Aldrich
Piperazine, ReagentPlus®, 99%
Supelco
1-Methylpiperazine, analytical standard
Sigma-Aldrich
StratoSpheres PL-MPH resin, 50-100 mesh, extent of labeling: 3.0-4.0 mmol/g loading, 1 % cross-linked
Sigma-Aldrich
Piperidine solution, suitable for peptide synthesis, 20% in DMF
Cyclizine impurity A, European Pharmacopoeia (EP) Reference Standard