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保护的氨烷基化亚磺酰双内酯的合成

付刚, 邹晓民, 傅翌秋, 牟科, 马超, 吕扬, 徐萍*   

  1. 北京大学药学院 天然药物及仿生药物国家重点实验室, 北京 100083
  • 收稿日期:2007-02-16 修回日期:2007-05-10 出版日期:2007-06-15 发布日期:2007-06-15
  • 通讯作者: 徐萍*

Synthesis of protected aminoalkyl sulfinyl dilactones from α-amino acids

Gang Fu, Xiao-Min Zou, Yi-Qiu Fu, Ke Mou, Chao Ma, Yang Lu, Ping Xu*   

  1. Department of Medicinal Chemistry, State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China
  • Received:2007-02-16 Revised:2007-05-10 Online:2007-06-15 Published:2007-06-15
  • Contact: Ping Xu*

摘要: 目的 合成了带有保护基的氨基烷基亚磺酰双内酯,此类化合物是一种有用的化学反应中间体,并且有可能作为蛋白酶体抑制剂的药效团。方法 综合使用多种有机合成反应,包括还原反应、氧化反应、Wittig烯化反应、氧化成邻二醇的反应等。结果 探索出一种合成保护的氨烷基化亚磺酰双内酯化合物的方便方法,此方法也适用于合成其他取代基的五元或六元环亚磺酰双内酯。结论 从四种不同的带有保护基的氨基酸合成了四个带有保护基的氨烷基亚磺酰双内酯。

关键词: 蛋白酶体抑制剂, 蛋白酶体抑制剂, 蛋白酶体抑制剂, 保护的氨烷基亚磺酰双内酯, 保护的氨烷基亚磺酰双内酯, 保护的氨烷基亚磺酰双内酯, 合成, 合成, 合成

Abstract: Aim To synthesize protected aminoalkyl sulfinyl dilactones which were useful as the synthetic intermediates or the Cterminal pharmacophores of potential peptidomimetic proteasome inhibitors. Methods Organic reactions such as reduction, oxidation, olefination, and dihydroxylation were used. Results A convenient synthetic procedure to afford a series of aminoalkyl sulfinyl dilactones was presented, which would be useful in the synthesis of five- or six-member sulfinyl dilactones. Conclusion Four aminoalkyl sulfinyl dilactones connecting different α-amino acids were synthesized.

Key words: Proteasome inhibitors, Proteasome inhibitors, Protected aminoalkyl sulfinyl dilactone, Protected aminoalkyl sulfinyl dilactone, Synthesis, Synthesis

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Supporting: Foundation item: National Natural Science Foundation of China (20572006), and 985 Program, Ministry of Education of China.
*Corresponding author. Tel.: 86-10-82801505; fax: 86-10-62015584