Abstract
A novel series of substituted 2-thiohydantoin incorporated with benzoimidazole, pyrazole, triazole and/or benzoxazole moieties has been synthesized using (E)-3-[1-(4-bromophenyl)ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material. The key material 1 also, reacted with an acetic anhydride, aromatic aldehydes, secondary amines, formaldehyde and triethyl orthoformate to give the corresponding acetyl, chalcone, Mannich bases and ethoxymethylene derivatives, respectively. The structures of the novel compounds were confirmed by spectral data and elemental analysis. The cytotoxic activity of all synthesized compounds was assessed in vitro against human hepatocellular cancer cell line (HePG-2) and breast carcinoma cell line (MCF-7). The bioassay results revealed that compound 14 has the best activity against HePG-2 cell line (IC50 = 2.33 μg/mL), while compound 5 has the best activity against MCF-7 cell line (IC50 = 3.98 μg/mL).
Highlights
A novel series of substituted 2-thiohydantoin incorporated with benzoimidazole, pyrazole, triazole and/or benzoxa‐ zole moieties has been synthesized using (E)-3-[1-(4-bromophenyl)ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material
As an extension of our work on the synthesis of heterocyclic systems and evaluation of their biological activity [27–33], we reported here the synthesis of some novel substituted 2-thiohydantoin and evaluate their cytotoxic activity. (E)-3-[1-(4-bromophenyl) ethylideneamino]-2-thioxoimidazolidin-4-one 1 was prepared and used as the building block for the synthesis of the novel compounds
Chemistry As an extension of our interest on the chemistry of 2-thiohydantoin, we reported here the synthesis of Elhady et al Chemistry Central Journal (2018) 12:51 novel derivatives using (E)-3-[1-(4-bromophenyl) ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material
Summary
A novel series of substituted 2-thiohydantoin incorporated with benzoimidazole, pyrazole, triazole and/or benzoxa‐ zole moieties has been synthesized using (E)-3-[1-(4-bromophenyl)ethylideneamino]-2-thioxoimidazolidin-4-one 1 as the key starting material. The resulting data of the 50% inhibition concentration (IC50) summarized in Table 7 showed that, the synthesized compounds have different activity against hepatocellular carcinoma cell line HePG2 and breast cancer cell line MCF-7.
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