Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives)

A series of 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives were synthesized by the cyclization of novel 2-(quinolin-8-yloxy) acetohydrazones. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that all the 2-(quinolin-8-yloxy) acetohydrazones were more active than their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). SAR showed that the compounds having quinoline ring and hydrazone linkage with free N–H group are responsible for higher antiamoebic activity. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were nontoxic at the concentration range of 1.56–50 μM.

Graphical abstractNovel 1,2,3-thiadiazole, 1,2,3-selenadiazole and 2-(quinolin-8-yloxy) acetohydrazone derivatives (2–19) were synthesized. Compounds (2–7), 9, 10, 12, 16 and 17 exhibited better antiamoebic activity and screened for cytotoxicity.Figure optionsDownload full-size imageDownload as PowerPoint slide