Thiol型Thiamine新誘導体の合成と反応(第2報)

概要

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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.
公益社団法人日本薬学会の論文
1973-11-25