Evaluation of Cytotoxic Properties of N,N ' -bis[(1-aryl-3-heteroaryl)propylidene]-hydrazine dihydrochlorides
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Pharmaceutical Chemistry Journal, Vol. 54, No. 8, November, 2020 (Russian Original Vol. 54, No. 8, August, 2020)
EVALUATION OF CYTOTOXIC PROPERTIES OF N,N¢-BIS[(1-ARYL-3-HETEROARYL)PROPYLIDENE]HYDRAZINE DIHYDROCHLORIDES K. Kucukoglu,1,* H. I. Gul,2 and H. Sakagami3 Original article submitted February 5, 2020. N,N¢-bis[(1-aryl-3-heteroaryl)propylidene]hydrazine dihydrochlorides, P1, P4 – P8, and R1 – R7, were assayed against human oral squamous cell carcinoma (HSC-2, HSC-3, HSC-4), human promyelocytic leukemia cell line (HL-60), and human normal oral cells (HGF, HPC, and HPLF) as non-tumor cells to evaluate their cytotoxic properties. Peplomycin was used as a reference compound. It was found that P- and R-series hydrazone compounds exhibited cytotoxicity in a range of 11 ± 0.68 – 300 ± 1.0 mM. Compound P1 which is a non-substituted hydrazone containing piperidine ring and compound R2 which is a 4-methyl hydrazone derivative containing pyrrolidine ring showed the most potent cytotoxic activity. These hydrazone compounds may serve as promising candidates for further studies. Keywords: cytotoxic activity, hydrazone, Mannich base, cancer, selectivity, anticancer drugs.
antibacterial [10], monoamine oxidase inhibitory [11], antiplatelet aggregation [12], and antiproliferative or anticancer [13 – 18] properties. Substrates having at least one active hydrogen atom, an aldehyde component (generally formaldehyde/paraformaldehyde), and an amine reagent react to form compounds generally known as Mannich bases. Mannich reactions are also known as aminoalkylation reactions since the obtained product is derivative of the substrate with an aminoalkyl moiety [19, 20]. Mannich bases are important pharmacophores and it is known that some compounds which are used today for clinical treatment of various diseases and disorders have this versatile scaffold, such as cocaine, fluoxetine, atropine, ethacrynic acid, procyclidine, trihexyphenidyl, ranitidine, and biperiden [21 – 23]. Furthermore, Mannich bases have different biological activities including antifungal [24 – 26], antimicrobial [27 – 29], anti-inflammatory [30 – 32], anti-HIV [33], carbonic anhydrase inhibition [34 – 40], cytotoxic and anticancer [18, 37, 40 – 50]. Previously, we have designed and synthesized some hydrazone compounds, N,N¢-bis[(1-aryl-3-heteroaryl)propylidene]hydrazine dihydrochlorides including P- and R-series via reaction of mono-Mannich bases, 1-aryl-3-heteroaryl-1-propanone, with hydrazine hydrate, evaluated their cytotoxic activity against human hepatoma (Huh7) and breast cancer (T47D) cell lines, and got some impressive results published in [16 – 18]. The present work was aimed to investigate the cytotoxic effect of synthesized compounds
1. INTRODUCTION Hydrazones having the chemical structure of R1R2C=NNH2 can be derived from a ketone or an aldehyde. If both R1 and R2 are aryl or alkyl, it indicates that hydrazone was derived from a ketone. Hydrazones are synthesized by the reaction of hydrazine with a ketone or an aldehyde. The oxygen atom of ketone o
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