Adrenochrome誘導体の研究(第1報)Adrenochrome Monosemicarbazoneの構造決定

概要

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Adrenochrome possesses >C=O group in the -5 and 6-positions but no synthetic evidence has been offered on which of these >C=O groups had reacted with semicarbazide to form adrenochrome monosemicarbazone. Catalytic reduction of the monosemicarbazone with palladium-carbon catalyst results in absorption of 1 mole of hydrogen to form 1-methyl-5-semicarbazido-6-hydroxyindole (II), whose methylation with dimethyl sulfate and sodium hydroxide affords 1-methyl-5-semicarbazido-6-methoxyindole (III). Pyrolysis of (III) by heating with sodium carbonate in glycerol at 185〜195° ended in liberation of nitrogen and 1-methyl-6-methoxyindole (IV) was formed. On the other hand, methylation of 6-methoxyindole (V) with methyl iodide in liquid ammonia with metallic sodium yielded (IV). This has proved that adrenochrome monosemicarbazone is 1-methyl-3-hydroxy-5-semicarbazono-6-oxo-2,3,5,6-tetrahydroindole.
公益社団法人日本薬学会の論文
1956-08-25