Synthesis, cytotoxicity and in vitro antibacterial screening of novel hydrazones bearing thienopyridine moiety as potent
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ORIGINAL PAPER
Synthesis, cytotoxicity and in vitro antibacterial screening of novel hydrazones bearing thienopyridine moiety as potent COX‑2 inhibitors Sherif M. H. Sanad1 · Ahmed E. M. Mekky1 Received: 24 March 2020 / Accepted: 26 June 2020 © Iranian Chemical Society 2020
Abstract The starting precursors 2-carbohydrazides, bearing thienopyridine moiety, were prepared using 2-thioxopyridine-3-carbonitriles as key synthons. Next, 2-carbohydrazides were reacted with a variety of 4-substituted benzylidinemalononitriles or 4-substituted benzaldehydes to afford a new series of the target hydrazones incorporating thienopyridine moiety. The elemental analyses and spectral data were used to demonstrate the structures of new hydrazones series. The in vitro antibacterial activities of the target hydrazones were evaluated against different strains of Gram-positive and Gram-negative bacteria. In comparison with chloramphenicol as a reference drug, hydrazones 13b, 13c and 13d, linked to p-Cl, p-Br and p-Me moiety, respectively, exhibited the strongest activities against all tested bacteria with MIC values in the range of 6.2–12.5 μg/mL. In addition, several new hydrazones were tested as in vitro cytotoxic agents against each of human breast carcinoma MCF-7 cell line, colon cancer Caco2 cell line and liver hepatocellular carcinoma HEPG2 cell line. The hydrazones 13b, 13c and 13d demonstrated the best cytotoxicity against the tested eukaryotic cells. Furthermore, both experimental and docking studies could predict the promising inhibitory activities of hydrazones 13c and 13d against COX-2 enzyme with IC50 of 0.110 and 0.104 µM, respectively, when compared with Celecoxib (IC50 of 0.115 µM). Graphic abstract
Keywords Hydrazones · Thieno[2,3-b]pyridine · In vitro antibacterial screening · COX-2 inhibitors · In silico study
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-01987-y) contains supplementary material, which is available to authorized users. * Sherif M. H. Sanad [email protected] 1
Chemistry Department, Faculty of Science, Cairo University, Giza 12613, Egypt
In recent years, design of synthetic routes for preparation of new thieno[2,3-b]pyridines has attracted considerable attention because of their important medicinal activities as antimicrobial [1, 2], antiviral [3, 4] and anti-inflammatory agents [5–7]. Also, these derivatives exhibit interesting antiproliferative and anticancer activities [8–11] as well as their capability for treatment of disorders of central nervous system [12–14]. Moreover, thienopyridines
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exhibit broad spectrum of bioactivities as antidiabetic [15, 16], antihypertensive [17, 18] and osteogenic [19, 20] activities. On the other hand, many publications reported the remarkable biological and pharmacological properties of several hydrazone containing derivatives as antituberculosis [21], antibacterial, antifungal [22–24], anticonvulsant [25], antimalarial [26] and anti-HIV [27] a
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