Studies with alkylating esters. VI. The chemical and biological activities of the isomers of dimethylmyleran

The meso- and (±)-isomers of dimethylmyleran (DMM) have been synthesised and their chemical reactivity towards selected nucleophiles has been investigated. Both isomers react in vitro by hydrolysis to give 2,5-dimethyltetrahydrofuran and with the thiol groups of cysteine, cysteine ethyl ester and glutathione forming 2,5-dimethyltetrahydrothiophene. As each of these cyclic compounds exists in the cis- and trans-configurations, their production in stereochemically quantitative yields from meso- and (±)-dimethylmyleran respectively, indicates that both isomers react by a bimolecular process and not a unimolecular one as has been generally accepted. A comparison of the activity of the isomers with that of Myleran on anti-fertility action, neutrophildepressant activity and effect on the weight response suggests that these esters could exert their biological actions in vivo by the same mechanism.