Development of approaches to fibrostatin F, N-acetyl-L-cysteinyl-containing 1,4-naphthoquinone metabolite of Streptomyces catenulae

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• 作者：Yu. E. Sabutskii ; V. A. Denisenko ; P. S. Dmitrenok…
• 关键词：Key wordsfibrostatins ; N ; acetyl ; L ; cysteine ; 5 ; hydroxy ; 2 ; 7 ; dimethoxy ; 3 ; methyl ; 1 ; 4 ; naphthoquinones ; N ; acetyl ; S ; [(8 ; hydroxy ; 3 ; 6 ; dimethoxy ; 1 ; 4 ; dioxonaphthalen ; 2 ; yl)methyl] ; Lcysteine ; Streptomyces catenulae
• 刊名：Russian Chemical Bulletin
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：65
• 期：3
• 页码：774-778
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry;
• 出版者：Springer US
• ISSN：1573-9171
• 卷排序：65

文摘

A possibility of the synthesis of microbial metabolite Streptomyces catenulae fibrostatin F through the AcOH-catalyzed condensation of 5-hydroxy-3-hydroxymethyl-2,7-dimethoxy1,4-naphthoquinone and its related 3-chloromethyl, 3-acetoxymethyl, and 3-methoxymethyl derivatives with N-acetyl-L-cysteine and paraformaldehyde in 1,4-dioxane was studied. In these conditions, all naphthoquinones gave N-acetyl-S-[(8-hydroxy-3,6-dimethoxy-1,4-dioxonaphthalen-2-yl)methyl]-L-cysteine isomeric to the natural fibrostatin C.