Abstract
The synthesis of thiosugars containing several diorganylarsino groups is described. The compounds prepared are: dihexadecyl-, di-n-octyl-, dicyclohexyl-, dibutyl-, dipropyl-, diethyl-, methyl-npropyl- and 2-hydroxyethylmethylarsino derivatives of 2,3 ,4 ,6 -tetra-0 - acetyl-l-thio- β-D-glucopyranose; dihexadecyl-, didodecyl-, di-n-octyl-, dicyclohexyl-, dibutyl-, dipropyl-, diethyl-, methyl-n-propyl- and 2-hydroxyethylmethylarsino derivatives of 1,2,3,4-tetra-0-acetyl-6- thio-B-D-glucopyranose; dibutyl-, dipropyl-, diethyl-, dimethyl- and 2-hydroxyethylmethylarsino derivatives of 3,4,6-tri-0-benzoyl-l-thio- 2-deoxy-β -D-glucopyranose; 1 ,3,4-tri-O-acetyl -6-S-dimethylarsino-6- thio-2-deoxy-B-D-glucopyranose; 3,4,6-tri-0-benzoyl-1-thio-2-deoxy-β-D-glucopyranose; and 1,3 ,4-tri-0-acetyl-6-thio-2-deoxy-β-D-glucopyranose. The compounds were characterized by proton and carbon-13 nuclear magnetic resonance spectrometry, mass spectroscopy and elemental analysis. All spectral data are consistent with the proposed structures of the compounds. The carcinostatic activity of these compounds is being tested by the National Cancer Institute and preliminary results have shown that the diethylarsino derivative of 1-thioglucose tetraacetate has the greatest activity of these types of compounds whereas the results on the dihexylarsino compounds are also rather promising. All compounds are being tested in vivo in mice with lymphocitic leukemia (PS 388).
Rosenthal, Maria Velazquez (1978). The synthesis and characterization of thio sugar esters of diorganylarsinous acids. Texas A&M University. Texas A&M University. Libraries. Available electronically from
https : / /hdl .handle .net /1969 .1 /DISSERTATIONS -229903.