YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
チオクト酸およびその関連化合物の合成研究 (第11報)
チオクト酸誘導体とビタミンB1との結合化合物の合成 その3
出口 義雄三浦 一子
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1963 年 83 巻 7 号 p. 708-713

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In continuation of previous works, attempt was made to synthesize a compound in which the sulfur atom at 6-position of thioctic acid was bonded in disulfide form to thiamine and the sulfur atom in 8-position was acetylated, i.e. methyl 8-acetylthio-6-{2-{N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]formamido}-1-(2-hydroxyethyl)propenyldithio}octanoate (IIIa). This compound, IIIa showed satisfactory result in thioctic acid activity and transition of its thiamine into blood cells. Among the various methods of synthesis tried, even that showing the highest yield gave the objective substance in a total yield of ca. 6% from methyl 8-chloro-6-hydroxyoctanoate (IV). It was found that the one of the reasons for this poor yield was the extremely slow reaction of the halogen atom in 6-position of methyl 8-acetylthio-6-halogenoöctanoate (VII) to form the Bunte salt (VIII) by the action of sodium thiosulfate and the fact that VIII is easily decomposed by heat.

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