Crystals (Dec 2020)

“Free of Base” Sulfa-Michael Addition for Novel <i>o-</i>Carboranyl-DL-Cysteine Synthesis

  • Julia Laskova,
  • Irina Kosenko,
  • Ivan Ananyev,
  • Marina Stogniy,
  • Igor Sivaev,
  • Vladimir Bregadze

DOI
https://doi.org/10.3390/cryst10121133
Journal volume & issue
Vol. 10, no. 12
p. 1133

Abstract

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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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