Total Synthesis of Amino‐Functionalized Calphostin Analogs as Potent and Selective Inhibitors of Protein Kinase C (PKC)

Bulletin of the Korean Chemical Society

Seung‐¹  Beom‐¹  Nam‐¹  Choon‐¹  Dae‐¹  Tae Kim²  Hyoyeon Kim²  Ho Song²  Jae Lee³  Gin Jung⁴  Hyuk Kim⁵ 

[1] 756 Korea;Department of Bioactive Material Sciences Center of Bioactive Materials Jeonju 561‐Department of Chemistry College of Natural Science Jeonju 561‐Department of Crop Science and Biotechnology College of Agriculture and Life Science Jeonju 561‐Department of Molecular Biology College of Natural Science Jeonju 561‐

关键词: Amino‐;    functionalized calphostin;    Naphthoquinone;    Perylenequinone;    Protein kinase C;   

DOI  :  10.1002/bkcs.10908

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

As potential protein kinase C (PKC) inhibitors and photodynamic agents, the novel amino‐functionalized calphostin analog 1,12‐bis((benzoyl‐amino)methyl)‐3,10‐perylenequinone was successfully prepared by dimerization of the key intermediate 3‐(benzoylamino)methyl‐1,2‐naphthoquinone (9), which was synthesized by an efficient and relatively short synthetic sequence (eight steps) with satisfactory overall yield. The naturally occurring form of perylenequinone 12 was prepared by consecutive methylation and demethylation reactions. In our synthetic strategy, it was beneficial that the amino functionality of 1,2‐naphthoquinone 9 could be easily introduced at an early synthetic stage and subsequently dimerized to prepare various potentially bioactive perylenequinones.

【 授权许可】

Unknown