Synthesis of new N, N′-bis[1-aryl-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides and evaluation of their cytotoxicity against human hepatoma and breast cancer cells. (June 2014)

• Record Type: Journal Article
• Authors: Kucukoglu, Kaan; Gul, H. Inci; Cetin-Atalay, Rengul; Baratli, Yosra; Charles, Anne-Laure; Sukuroglu, Murat; Gul, Mustafa; Geny, Bernard
• Is Part Of: Journal of enzyme inhibition and medicinal chemistry. Volume 29:Number 3(2014:Jun.)
• Page Start: 420
• Page End: 426
• Publication Date: 2014-06
• Subjects: Enzyme inhibitors -- Periodicals; Enzyme Inhibitors -- periodicals; Biochemistry -- periodicals; 572.7
• DOI: 10.3109/14756366.2013.795562
• Languages: English
• ISSNs: 1475-6366

Abstract

<abstract> <title>Abstract</title> <p>N, N′-Bis[1-aryl-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides were synthesized by the reaction of 2 mols of 1-aryl-3-(piperidine-1-yl)-1-propanone hydrochlorides with 1 mol of hydrazine hydrate. Aryl part was C<sub>6</sub>H<sub>5</sub> (<bold>P1</bold>), 4-CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub> (<bold>P2</bold>), 4-CH<sub>3</sub>OC<sub>6</sub>H<sub>4</sub> (<bold>P3</bold>), 4-HOC<sub>6</sub>H<sub>4</sub> (<bold>P4</bold>), 4-ClC<sub>6</sub>H<sub>4</sub> (<bold>P5</bold>), 3-CH<sub>3</sub>OC<sub>6</sub>H<sub>4</sub> (<bold>P6</bold>), 4-FC<sub>6</sub>H<sub>4</sub> (<bold>P7</bold>) and 4-BrC<sub>6</sub>H<sub>4</sub> (<bold>P8</bold>). Except <bold>P1</bold>, all compounds were reported for the first time. The chemical structures were confirmed by UV, <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS spectra. <bold>P1</bold>, <bold>P2</bold>, <bold>P7</bold> and <bold>P8</bold> against human hepatoma (Huh7) cells and <bold>P1</bold>, <bold>P2</bold>, <bold>P4</bold>, <bold>P5</bold>, <bold>P6</bold>, <bold>P7</bold> and <bold>P8</bold> against breast cancer (T47D) cells have shown cytotoxicity. <bold>P1</bold>, <bold>P2</bold> and <bold>P7</bold> had more potent cytotoxicity against Huh7 cells than the reference compound 5-FU, whereas only <bold>P2</bold> was more potent than the 5-FU against T47D cells. Representative compound <bold>P7</bold> inhibited the mitochondrial respiration at 144, 264 and 424 µM concentrations dose-dependantly in liver homogenates. The results suggest that <bold>P1</bold>, <bold>P2</bold>, <bold>P7</bold> and <bold>P8</bold> may serve as model compounds for further synthetic studies.</p> </abstract>