Thiolytic chemistry of alternative precursors to the major metabolite of the cancer chemopreventive oltipraz.

Navamal M, McGrath C, Stewart J, Blans P, Villamena F, Zweier J, Fishbein JC
J Org Chem. 2002 67 (26): 9406-13

PMID: 12492345 · DOI:10.1021/jo020588n

The compounds 7-methyl-6,8-bis(methyldisulfanyl)pyrrolo[1,2-a]pyrazine (5; "bis disulfide") and methanethiosulfonic acid S-((6-(methanesulfonylsulfanyl)-7-methyl)pyrrolo[1,2-a]pyrazin-8-yl) ester (6; "bis methanesulfonic acid thioester") have been synthesized to serve as alternative precursors to the major metabolite, 4, of the cancer chemopreventive oltipraz, 1, to test whether they possess similar biological activities. In the present work the mechanisms by which these compounds react with glutathione have been investigated in order to validate the assumption that they would be chemically competent in the presence of the biological thiols to give the oltipraz metabolite. A kinetic and product study was carried out in mainly aqueous media,

MeSH Terms (13)

Algorithms Anticarcinogenic Agents Chromatography, High Pressure Liquid Electron Spin Resonance Spectroscopy Free Radicals Glutathione Kinetics Models, Molecular Molecular Structure Pyrazines Sulfhydryl Compounds Thiones Thiophenes

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