Synthesis, structural characterization and antitumor activity of 2-(di-p-tolylstibano)- and 2-(di-p-tolylbismuthano)-N-p-tolylbenzamide

• Organoantimony and bismuth compounds with an amide moiety as the pendant arm were prepared.
• The analyses showed the presence of intramolecular interactions between the group 15 elements (Sb, and Bi) and oxygen.
• The organobismuth compound showed enhanced antitumor activity than the organoantimony compound in all the tested cell lines.

Novel organoantimony and bismuth compounds, 2-(di-p-tolylstibano)- and 2-(di-p-tolylbismuthano)-N-p-tolylbenzamide (2 and 3), bearing an amide moiety as the pendant arm were synthesized and characterized by NMR, IR, single-crystal X-ray diffraction, and elemental analyses. The molecular structures of compounds 2 and 3 showed the presence of intramolecular interactions between the antimony/bismuth and carbonyl oxygen atoms in the solid state, respectively. The central atoms (Sb and Bi) exhibited a pseudo trigonal bipyramidal structure. Compounds 2 and 3 showed potent antiproliferative activity in all the tested cell lines. In particular, compound 3 containing bismuth was more sensitive than compound 2 containing antimony.

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