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

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.(c) 2021 Elsevier B.V. All rights reserved.

Automated summary

Methodologies for synthesizing the first generation of 3-nitro-1,8-naphthalimides containing nido and closo moieties are reported. Boron-containing compounds were synthesized by reacting 3-nitro-1,8-naphthalic anhydride with ammonium derivatives of nido and closo ions. A novel boron-enriched mitonafide was obtained through nucleophilic ring-breakdown reaction. These synthesized compounds have potential as agents for boron neutron capture therapy for cancer.