Synthesis and biological screening of 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles as antiproliferative and anti-inflammatory agents

• Titled compounds were synthesized using DIB mediated oxidative cyclisation.
• Anti-inflammatory & anti-proliferative activities screened exhibit correlation.
• Compound 6i and 6t showed better inhibition of paw edema compared to standard.
• In vitro cytotoxicity evaluated against A-549, HeLa, HepG-2 and Du145 cancer cells.
• 6i, 6q and 6t are identified as good candidates against all the cancer cell lines tested.

A series of 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles were efficiently synthesized by oxidative cyclisation of N′-benzylidene-(1H-indol-3-yl)alkane hydrazides using di(acetoxy)iodobenzene. N′-Benzylidene-(1H-indol-3-yl)alkane hydrazides themselves were derived from simple indole-3-carboxylic acids. The 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles were evaluated for their anti-inflammatory and anti-proliferative activities. Based on the results obtained structure and activity relationship (SAR) was established and a correlation between the activities was observed. Compound 6i and 6t showed best activity against proliferation of human cancer cell lines and as well as inflammation of rat paw edema.

A series of 5-(alkyl(1H-indol-3-yl))-2-(substituted)-1,3,4-oxadiazoles were synthesized and evaluated for anti-proliferative activity against four different cancer cell lines and anti-inflammatory activity. A correlation between the anti-proliferative and anti-inflammatory activities has been established.Figure optionsDownload as PowerPoint slide