Biomolecules containing the SAsR₂ functional group : a chemical and carcinostatic study

Abstract

Thio sugar and thio steroid esters of several dialkylarsinous acids have been prepared and characterized. Specifically, the syntheses of the following compounds have been investigated: 1-thio-2,3:5,6-di-O-isopropylidene mannofuranose; 1-S-dialkylarsino-1-thio-2,3:5,6-di-O-isopropylidene-mannofuranoside, (alkyl = methyl, ethyl, propyl, and butyl); 6-thio-1,2,3,4-tetra-O-acetyl-mannopyranoside; 6-S-alkylarsino-6-thio-1,2,3,4-tetra-O-acetyl-mannopyranoside, (alkyl = methyl, ethyl, propyl, and butyl); 3-thio-dehydroisoandrosterone; 3-S-dialkylarsino-3-thio-dehydroisoandrosterone, (alkyl = methyl, ethyl, propyl, and butyl); Pregn-4-ene-1,16-dithio-21-acetyl-3,11,20 trione; Pregna-1,4-diene-16-S-dialkylarsino-16-thio-21-acetyl-3,11,20-trione, (alkyl = methyl, ethyl); 24-thio-lanosterol; 24-S-dialkylarsino-24-thio lanosterol, (alkyl = methyl, ethyl). Attempted preparations are also reported for 17-S-dialkylarsino-17-thio-testosterone and 17-S-dialkylarsino-17-thio-cortisone acetate. The [^1}H NMR spectrum of these compounds may be interpreted in a manner consistent with the proposed structures. [^13]C NMR spectra were reported and used to elucidate the structure of the dehydroisoandrosterol. The mass spectra of the compounds are reported...