Design, structural and spectroscopic elucidation and in vitro antimicrobial, anticancer, antileishmanial, urease inhibition activities and interaction with SS-DNA of newly synthesized amide based carboxylic acid

• Synthesis of novel compound.
• Structural and spectroscopic characterization.
• Antimicrobial activities.
• Anticancer, antileishmanial and urease inhibition activities.
• Interaction with SS-DNA via intercalative mode of interaction.

N-[(4-methoxyphenyl)]-4-oxo-4-[oxy]butanamide was synthesized and characterized by various techniques like elemental analyses, FT-IR, NMR (1H, and 13C), mass spectrometry and single crystal X-ray structural analysis. The appearance of the OH peak of the carboxylic acid in the FT-IR and NMR spectra conform the formation of the compound. The molecular structure of the compound is stabilized by short intramolecular O–H⋯O hydrogen bonds within the molecule. The synthesized compound was screened for in vitro biological activities like antimicrobial, anticancer, antileishmanial activities as well as interaction with SS-DNA (Salmon sperm DNA). It shows good antimicrobial activity. The in vitro anticancer activity against lung carcinoma (H157) and Vero cell lines demonstrate that the synthesized compound has almost comparable activity to that of the standard anticancer drug, vincristine. The biological importance of the compound is that it has almost no effect (less than 26.7%) on the normal cell line, Vero cell line. It was also tested for antileishmanial activity against the promastigote form of leishmania major and obtained attractive result. It was also tested for urease inhibition and showed good inhibitory activity against jack bean urease (IC50 = 4.08 ± 2.54 μM). UV–Vis spectroscopic result reveals that the binding mode of interaction of the compound with SS-DNA is intercalative DNA interaction and the intercalative mode of interaction was further supported by viscometry.

The compound inserts into the base pairs of DNA while interacting via intercalative mode. It also show good antimicrobial, anticancer, antileishmanial and urease inhibition activities.Figure optionsDownload as PowerPoint slide