'Free of Base' Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis

Autor: Julia Laskova, Irina Kosenko, Ivan Ananyev, Marina Stogniy, Igor Sivaev, Vladimir Bregadze
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Crystals, Vol 10, Iss 12, p 1133 (2020)
Druh dokumentu: article
ISSN: 2073-4352
DOI: 10.3390/cryst10121133
Popis: The sulfa-Michael addition reaction was applied for the two-step synthesis of o-carboranyl cysteine 1-HOOCCH(NH2)CH2S-1,2-C2B10H11 from the trimethylammonium salt of 1-mercapto-o-carborane and methyl 2-acetamidoacrylate. To avoid the decapitation of o-carborane into its nido-form, the “free of base” method under mild conditions in a system of two immiscible solvents toluene-H2O was developed. The replacement of H2O by 2H2O resulted in carboranyl-cysteine containing a deuterium label at the α-position of the amino acid 1-HOOCCD(NH2)CH2S-1,2-C2B10H11. The structure of the protected o-carboranyl cysteine was determined by single-crystal X-ray diffraction. The obtained compounds can be considered as potential agents for the Boron Neutron Capture Therapy of cancer.
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