Synthesis of naphthalimide derivatives of closo‑dodecaborate and nido‑carborane

Abstract

Methodologies for the synthesis of the first 3-nitro-1,8-naphthalimides bearing the nido‑carborane and closo‑dodecaborate moieties are reported. Series of boron containing 3-nitro-1,8-naphthalimides were synthesized by the reaction of 3-nitro-1,8-naphthalic anhydride with ammonium derivatives of nido‑carborane and closo‑dodecaborate anions. The nucleophilic ring-breakdown reaction of cyclic oxonium derivatives of nido‑carborane with the tertiary dimethylamino group of mitonafide led to the novel boron-enriched mitonafides. The synthesized compounds are of interest as potential agents for boron neutron capture therapy for cancer.