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

Design of DNA Intercalators Based on 4-Carboranyl-1,8-Naphthalimides: Investigation of Their DNA-Binding Ability and Anticancer Activity

“…Additionally, J. Laskova et al classically obtained 3-nitro-1,8-naphthalimides bearing the nido-carborane and closo-dodecaborate modifications by reaction of naphthalic anhydride with ammonium derivatives containing a boron cluster. A mitonafide derivative modified with nido-carborane was obtained using the nucleophilic ring-opening reaction of the corresponding cyclic oxonium derivatives [10]. However, physicochemical and biological studies on this group of compounds have not been performed.…”

Synthesis and Reactivity of Cyclic Oxonium Derivatives of nido-Carborane: A Review

“…Later, it was found that the reaction of nido-carborane with HgCl 2 in tetrahydrofuran leads to the selective formation of the symmetrically substituted product 10-(CH 2 ) 4 O-7,8-C 2 B 9 H 11 [60,61]. In a similar way, the derivatives with 1,4-dioxane 10-O(CH 2 CH 2 ) 2 O-7,8-C 2 B 9 H 11 [60] and tetrahydropyran 10-(CH 2 ) 5 O-7,8-C 2 B 9 H 11 [62,63] were synthesized.…”

“…The reactions of 1,4-dioxane [63,71] and tetrahydropyran [63] derivatives of nidocarborane with ammonia in tetrahydrofuran led to the corresponding ammonium derivatives of nido-carborane. The obtained compounds were used for the conjugation with 3-nitro-1,8-naphthalic anhydride in the presence of Et 3 N to give water-soluble boron containing 3-nitro-1,8-naphthalimides, which are potential interesting agents for boron neutron capture therapy [63] (Scheme 14). Scheme 14.…”

“…The molecular structure of 10-NH 3 CH 2 CH 2 OCH 2 CH 2 O-7,8-C 2 B 9 H 11 was determined by single crystal X-ray diffraction [71] (Figure 4). The charge-compensated nido-carborane-based conjugates with mitonafide were prepared in mild conditions by the ring-opening reactions of 1,4-dioxane and tetrahydropyran derivatives of nido-carborane with dimethylamino group of mitonafide [63] (Scheme 15). The dimethyl-and diethyloxonium derivatives of nido-carborane are also easily reacted with nucleophiles with the loss of the methyl or ethyl group, respectively, and can be used as alkylating agents [72,73].…”

Charge-compensated nido-carborane derivatives in the synthesis of iron(ii) bis(dicarbollide) complexes

“…All reactions were carried out under an argon atmosphere. [FeCl 2 (dppe)], 54 K[7,8-C 2 B 9 H 12 ], 55 [10-EtC(NHR)HN-7,8-C 2 B 9 H 11 ] (R = Pr ( 1 ), Ph ( 2 )) 33 a and [10-EtC(NHR)HN-7,8-C 2 B 9 H 11 ] (R = (CH 2 ) 2 OH ( 3 ), (CH 2 ) 3 OH ( 4 ), (CH 2 ) 2 NMe 2 ( 5 )), 33 b [10-EtCN-7,8-C 2 B 9 H 11 ] ( 11 ), 39 [10-C 4 H 8 O-7,8-C 2 B 9 H 11 ] ( 13 ), 56 [10-O(CH 2 CH 2 ) 2 O-7,8-C 2 B 9 H 11 ] ( 14 ), 56 [10-C 5 H 10 O-7,8-C 2 B 9 H 11 ] ( 15 ) 57 and [10-Et 2 O-7,8-C 2 B 9 H 11 ] ( 16 ) 43 b were prepared according to the literature procedures. Anhydrous FeCl 2 and t -BuOK were purchased from Sigma-Aldrich and Acros Organics, correspondently.…”