Abstract
BackgroundChalcones have a place with the flavonoid family and show a few very important pharmacological activities. They can used as initial compounds for synthesis of several heterocyclic compounds. The compounds with the backbone of chalcones have been reported to possess various biological activities.ResultsPyridine and thioamide derivatives were obtained from the reaction of 3-(furan-2-yl)-1-(p-tolyl)prop-2-en-1-one with the appropriate amount of malononitrile, benzoylacetonitrile, ethyl cyanoacetate and thiosemicarbazide in the presence of ammonium acetate. The reaction of 3,5-di(furan-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide with ethyl 2-chloro-3-oxobutanoate, 3-chloropentane-2,4-dione or ethyl chloroacetate produced thiazole derivatives. Pyrano[2,3-d]thiazole derivatives were obtained as well from thiazolone to arylidene malononitrile. The structures of the title compounds were clarified by elemental analyses, and FTIR, MS and NMR spectra. Some compounds were screened against various microorganisms (i.e., bacteria +ve, bacteria −ve and fungi). We observed that compounds (3a), (4a), (4d), (5), (7) and compound (8) exhibited high cytotoxicity against the MCF-7 cell line, with IC50 values of 23.6, 13.5, 15.1, 9.56, 14.2 and 23.5 μmol mL−1, respectively, while compound (9) was displayed the lowest values against MCF-7 cell lines.ConclusionsEfficient synthetic routes for some prepared pyridines, pyrazoline, thioamide, thiazoles and pyrano[2,3-d]thiazole were created. Moreover, selected newly-synthesized products were evaluated for their antitumor activity against two carcinoma cell lines: breast MCF-7 and colon HCT-116 human cancer cell lines.
Highlights
Chalcones have a place with the flavonoid family and show a few very important pharmacological activities
In continuation of our previous work on the synthesis of new anticancer agents [29,30,31,32,33,34], we present here efficient syntheses of novel pyridines, pyrazolines, thiazoles and pyrano[2,3-d]thiazole derivatives which have not been previously reported
We investigated the anticarcinogenic effects against estrogen responsive prolifera‐ tive breast cancer model (MCF-7), and the antibacterial activity of HCT-116 on human cancer cell lines against Streptococcus pneumonia and Bacillus subtilis as examples of Gram-positive bacteria and Pseudomonas aeruginosa and Escherichia coli as examples of Gram-negative bacteria
Summary
Chalcones have a place with the flavonoid family and show a few very important pharmacological activities They can used as initial compounds for synthesis of several heterocyclic compounds. The chalcones (1,3-diaryl-2-propenones) and their derivatives are important intermediates in organic synthesis [1,2,3]. They serve as starting material for the synthesis of a variety of heterocyclic compounds of physiological importance. Pyrano[2,3-d]thiazoles are biologically interesting compounds with diabetes, obesity, hyperlipidemia, and atherosclerotic diseases [26]. They are known to show antimicrobial, bactericidal, fungicidal and molluscicidal activities [27, 28]. We investigated the anticarcinogenic effects against MCF-7, and the antibacterial activity of HCT-116 on human cancer cell lines against Streptococcus pneumonia and Bacillus subtilis as examples of Gram-positive bacteria and Pseudomonas aeruginosa and Escherichia coli as examples of Gram-negative bacteria
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