Design, synthesis and characterization of picoline based organoselenium compounds, 1,2-bis(pyridine-2/3/4-yl)methyl diselanes: X-ray crystal structure of 1,2-bis(pyridine-3-yl)methyldiselane

• Synthesis of 1,2-bis(pyridinyl)methyldiselanes by reductive selenation is reported.
• Base-catalyzed reductive selenation was carried out using sodium hydrogen selenide.
• Current protocol affords high yields under mild conditions, avoiding toxic H2Se.
• Anti-proliferative activity of diselanes against cancer and pathogenic cells studied.
• Structure elucidation of 1,2-bis(pyridine-3-yl)methyldiselane by X-ray crystallography.

An efficient synthetic protocol affording symmetrical 1,2-bis(pyridine-2/3/4-yl)methyldiselanes from pyridine-2/3/4-carbaldehyde in high yields at room temperature, without using highly toxic hydrogen selenide, has been developed. The synthesis involves the reductive selenation of pyridine-2/3/4-carbaldehyde with sodium hydrogen selenide, NaHSe in the presence of piperidine hydrochloride followed by NaBH4 reduction under mild conditions. Primary screening of the anti-proliferative activity of the newly synthesized compounds against several mammalian cell lines and pathogenic strains has been carried out. The crystal structure of 1,2-bis(pyridine-3-yl)methyldiselane has been established by X-ray diffraction analysis.

Crystal structure of 1,2-bis(pyridine-3-yl)methyldiselane.Figure optionsDownload as PowerPoint slide