Reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide: Studies related to the reaction of antitumor antibiotic leinamycin with DNA

Article abstract of DOI:10.1021/jo00118a010

We have studied the reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide. The major products isolated from these reactions are the corresponding dithio carboxylic acids. In the case of 3H-1,2-benzodithiol-3-one 1-oxide, an unstable hydrodisulfide that decomposes to polysulfides under the reaction conditions is formed. A mechanism involving an unstable oxathiolanone intermediate is proposed for these reactions. We believe that these reactions may serve as useful models for some aspects of the thiol-activated DNA-cleavage chemistry of the antitumor antibiotic leinamycin, a natural product that contains a 1,2-dithiolan-3-one 1-oxide heterocycle.