Synthesis of Actinomycin Related Compounds. I

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Amino acid derivatives bearing an actinomycin chromophore was synthesized in a hope of finding one or another with more carcinolytic activity and less toxicity than the actinomycin. That is, DL-valine ethylester, DL-serine ethylester, DL-phenylalanine ethylester, α-aminocaprolactam, 3-aminopiperidone (2), and 3-aminopyrrolidone (2) were acylated with 3-benzyloxy-4-methyl-2-nitrobenzoyl chloride. These compounds were catalytically hydrogenated to 3-hydroxy-4-methylanthraniloyl derivatives and then oxidized to actinocyl derivatives. In the course of these investigation, it was observed that dehydric cyclization occurs between carboxyl and amino group when 3-benzyloxy-4-methyl-2-nitrobenzoyl-L-proline is hydrogenated. Similar dehydric cyclization were observed in hydrogenation process of 3-benzyloxy-4-methyl-2-nitrobenzoyl-L-hydroxyproline and o-nitrobenzoyl-L-proline.

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