Total synthesis of orychophragine D via intramolecular Mitsunobu reaction and its radioprotective activity

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-08-27 DOI:10.1016/j.tet.2025.134902

Chun-Bo Ge , Si-Fan Liu , Zhi-Yan Zhang , Rui-Hong Li , Min Li , Zi-Ming Xia , Bin Li , Ying Tian , Guang-Jie Zhang , Shu-Chen Liu

引用次数: 0

Abstract

Orychophragine D (14) was an alkaloid, with a novel piperazine [1,2-a] [1,3,5] triazine molecular skeleton, obtained from the seeds of Orychophragmus violaceus. Previous studies had revealed the excellent radiation protection activity of 14. In this study, the total synthesis of 14 was achieved for the first time. An intramolecular Mitsunobu reaction was applied in this study, where alcohol and nucleophile required for the reaction were cleverly integrated into one molecule. Moreover, the radioprotective activity of the synthesized 14 was verified, which increased the survival rate of HUVEC irradiated with a radiation dose of 15 Gy from 55.9 % to 75.1 %.

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分子内Mitsunobu反应合成羊藿苷D及其辐射防护活性

Orychophragine D（14）是从Orychophragmus violaceus种子中提取的一种具有新型哌嗪[1,2-a][1,3,5]三嗪分子骨架的生物碱。以前的研究表明，14的优良的辐射防护活性。本研究首次实现了其中14的全合成。本研究采用分子内光信反应，将反应所需的醇和亲核试剂巧妙地整合到一个分子中。并验证了合成的14的辐射防护活性，使15 Gy辐照下HUVEC的存活率由55.9%提高到75.1%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.