多组分环氮杂过氧化物的组装由钐配合物催化及其细胞毒性活性。

Multicomponent Assembly of Bicyclic Aza-peroxides Catalyzed by Samarium Complexes and Their Cytotoxic Activity.

机构信息

Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prospekt Oktyabrya, 450075 Ufa, Russian Federation.

N.D. Zelinsky Institute of Organic Chemistry, 47, Leninsky prospekt, 119991 Moscow, Russian Federation.

出版信息

J Org Chem. 2023 Aug 18;88(16):11473-11485. doi: 10.1021/acs.joc.3c00555. Epub 2023 Aug 9.

DOI:10.1021/acs.joc.3c00555

PMID:37557189

Abstract

An original strategy toward bridged tetraoxazaspirobicycloalkanes was developed. The synthesis is based on a three-component condensation-cyclization reaction of primary arylamines with 1,1'-peroxybis (1-hydroperoxycycloalkanes) and pentane-1,5-dial catalyzed by Sm(NO)·6HO. The structures and conformations of the products were determined by X-ray diffraction analysis and H and C NMR spectroscopy. High cytotoxic activity and biological potential toward ferroptosis induction were found for the synthesized bicyclic aza-peroxides.

摘要

一种桥连四氧杂氮杂环丁烷的原创策略被开发出来。该合成基于伯芳胺与 1,1'-过氧化双(1-过氧环烷烃)和戊烷-1,5-二醛在 Sm(NO)·6HO 催化下的三组分缩合-环化反应。产物的结构和构象通过 X 射线衍射分析和 H 和 C NMR 光谱确定。所合成的双环氮杂过氧化物表现出高细胞毒性活性和诱导铁死亡的生物潜力。