Syntheses and Reactions of New Thiol-type Thiamine Derivatives. II

Abstract

Reaction of N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-N-[4-hydroxy-1-methyl-2-(dialkylaminodithio)-1-butenyl] formamides (I) (thiamine dialkylamino disulfides) with alkanethiols in ethanol containing 2 moles of hydrogen chloride gave N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-N-[4-hydroxy-1-methyl-2-(alkyltrithio)-1-butenyl] formamides (II) (thiamine alkyl trisulfides) in a high yield. The mechanism of this reaction was studied and discussed. When the propyl derivative (IIa) was treated with cycteine, thiamine (IX) and S-(propyldithio) cysteine (XI) were obtained. On the other hand, treatment of 1-adamantyl derivative (IId) with cysteine gave IX, cystine, and bis (1-adamantyl) tetra-sulfide (XII). II showed full thiamine activity in growth-promoting assay using thiamine-deficient rats.