DIMETHYLARSINOUS ACID ESTERS OF 1-THIO- AND -SELENOGALACTOSE. A NEW CLASS OF POTENTIAL CARCINOSTATIC AGENTS

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Abstract
The syntheses of 2,3,4,6-tetra-O-acetyl-1-S-dimethylarsino-1-thio-β-D-galactopyranose (4), 1-S-dimethylarsino-1-thio-β-D-galactopyranose (5), and 2,3,4,6-tetra-O-acetyl-1-Se-dimethylarsino-1-seleno-β-D-galactopyranose (8) are reported. An attempted preparation of 1-Se-dimethylarsino-1-seleno-β-D-galactopyranose (10) is also described. The compounds were characterized by nmr, uv, and mass spectroscopy, as well as elemental analysis. The 1H nmr spectra of these compounds were not exceptional except for the slight down-field shift of the –AsMe2 resonance noted in the selenium derivative as compared to the sulfur compound. Ultraviolet spectra of these compounds showed a relatively intense absorption which can be attributed to an n → o∗ transition associated with the As–X (X = S, Se) bond. The Δmax for the Se compounds show a slight red shift relative to analogous S compounds. The mass spectra of these compounds showed immediate loss of the aglycon, –XAsMe2, in all cases. Other fragments can be ascribed to subsequent fragmentation of the sugar portion of the molecule. Biochemical testing was carried out on compounds 4 and 5 and both displayed carcinostatic activity against mouse lymphocytic leukemia. A hypothesis is advanced to account for the observed carcinostatic action of dimethylarsino compounds as a group.