Collect. Czech. Chem. Commun. 2002, 67, 1095-1108

A Novel Approach to the Syntheses of Functionalized, Water-Soluble Icosahedral Carboranyl Anions. Crystal Structure of Methyl N-[(Trimethylamineboryl)carbonyl]-L-tyrosinate: A Synthon for Novel Carboranylpeptides

Bernard F. Spielvogela, Geeta Ranaa, Kamesh Vyakaranama, Kurt Grelcka, Kari E. Dickea, Bridget D. Dolasha, Shou-Jian Lia, Chong Zhenga, John A. Maguireb, Masao Takagakic and Narayan S. Hosmanea,*

a Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, U.S.A.
b Department of Chemistry, Southern Methodist University, Dallas, Texas 75275-0314, U.S.A.
c Research Reactor Institute, Kyoto University, Osaka, Japan


New functionalized water-soluble carboranyl anions have been prepared from ortho-carborane through lithiation and subsequent derivatization. The reaction of Li2[1,2-C2B10H10] with Me3NBH2X produced the carboranylborane dianions, [1,2-(BH2X)-1,2-C2B10H10]2- (X = H (2a), CN (2b), COOMe (2c), COOH (2d)), while the reaction of [1-R-2-Li-C2B10H10]- with Me3NBH2X produced the monoanions [1-R-2-BH2X-C2B10H10]- (R = C6H5, X = H (2e), CN (2f), COOH (2h), COOCH3 (2g), CONHCH(CH2OH)COOMe (2i), CONHCH(CHMe2)COOMe (2j), CONHCH(4-CH2C6H4OH)- COOMe (2k); R = Me, X = H (2l), COOH (2m)). These water-soluble carboranylboranes have the potential of being effective hydrophilic boron neutron capture therapy (BNCT) agents. The crystal structure of the peptide precursor Me3NBH2CONHCH(4-CH2C6H4OH)COOMe (3b) which showed a special promise as a BNCT agent is also described.

Keywords: Carboranes; Boron neutron capture therapy; BNCT; Amino acids; Amineboranes; Peptides.

References: 30 live references.