Synthesis of bipyridine‐linked dimers of azanonaborane: electronic absorption and molecular‐orbital calculations

El‐Zaria, Mohamed E.; Borrmann, Tobias; Gabel, Detlef

doi:10.1002/aoc.434

Cited by 3 publications

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“…For the other compounds, the mass spectra show the equivalent isotope patterns. The color of the compounds 2-8 might be due to the electronic interaction between the boron cluster unit and the bonded pyrimidine unit, as has been found for the monopyridine or bipyridine compounds [30,31]. This phenomenon may be related to that found for other borane pyridine complexes, particularly those of the {6,9-L2-arachno-B 10 H 12 } constitution [32].…”

Section: Resultsmentioning

confidence: 52%

“…The exo amine ligand (RNH 2 ) can be readily replaced with other primary or secondary amines [29]. Aliphatic amines can be replaced with pyridine [30,31] or imidazole [26] derivatives. In line with these results, we found it is possible to exchange the RNH 2 group with purine or purine derivatives to synthesize new azanonaborane clusters containing a purine moiety.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

2008

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Derivatives of purine, adenine, guanine, and 2,6-diaminopurine linked to the azanonaborane (B 8 N cluster) have been prepared, for possible use as powerful agents for boron neutron capture therapy (BNCT). The synthesis was carried out via a ligand exchange reaction. The exo-NH 2 R group of the azanonaborane of the type [(RH 2 N)B 8 H 11 NHR] can be exchanged by one hetero-nitrogen atom of the pyrimidine ring, and except for guanine, also by an N atom of the imidazole ring. The identity of the products was confirmed by NMR, elemental analysis, IR, and mass spectrometry. No reaction was found to occur with caffeine and theophylline under the same reaction conditions.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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Section: Resultsmentioning

confidence: 52%

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

2008

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Azanonaboranes Containing Imidazole Derivatives for Boron Neutron Capture Therapy: Synthesis, Characterization, and In Vitro Toxicity Evaluation

El‐Zaria

Genady

Gabel

2006

Chemistry A European J

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A number of azanonaboranes containing imidazole derivatives have been synthesized by a ligand-exchange reaction. The exo-NH(2)R group of the azanonaborane of the type [(RH(2)N)B(8)H(11)NHR] can be exchanged by one hetero-nitrogen atom of the imidazole ring. In the case of histamine, the exchange takes place on the aliphatic amino group, the hetero-nitrogen atom of the imidazole ring or both of them. The products were confirmed by NMR, IR spectroscopy, elemental analysis, and mass spectrometry. The electron-withdrawing effect of the nitro group in 2-nitroimidazole is the main hindrance to achieve the exchange reaction. In vitro experiments were performed with B16 melanoma cells. A comparison of the biological properties of the products in which the B(8)N cluster is connected to the hetero-nitrogen atom of imidazole ring or the aliphatic NH(2) group showed that incorporation of B(8)N cluster unit into primary amino group increases the compound's toxicity. In contrast, this specificity for cytotoxicity effect was not observed in the case of histamine containing two B(8)N clusters which was relatively nontoxic and did not inhibit colony formation up to concentrations of 2 mM.

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Synthesis of boron-containing heterocyclic compounds

Azev

Slepukhina

Gabel

2004

Applied Radiation and Isotopes

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Synthesis of bipyridine‐linked dimers of azanonaborane: electronic absorption and molecular‐orbital calculations

Cited by 3 publications

References 18 publications

Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

Azanonaboranes Containing Imidazole Derivatives for Boron Neutron Capture Therapy: Synthesis, Characterization, and In Vitro Toxicity Evaluation

Synthesis of boron-containing heterocyclic compounds

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