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氧化钒(V)希夫碱配合物来源于手性 3-氨基-1,2-丙二醇对映异构体:合成、光谱研究、催化和生物活性。

Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity.

机构信息

Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, PL-80308 Gdansk, Poland.

Department of Pharmaceutical Pathophysiology, Faculty of Pharmacy, Medical University of Gdansk, Dębinki 7, Building 27, PL-80211 Gdansk, Poland.

出版信息

Int J Mol Sci. 2024 May 3;25(9):5010. doi: 10.3390/ijms25095010.

Abstract

Oxidovanadium(V) complexes, and , with chiral tetradentate Schiff bases, which are products of monocondensation of (‒)-3-amino-1,2-propanediol or (+)-3-amino-1,2-propanediol with salicylaldehyde derivatives, have been synthesized. Different spectroscopic methods, viz. H and V NMR, IR, UV-Vis, and circular dichroism, as well as elemental analysis, have been used for their detailed characterization. Furthermore, the epoxidation of styrene, cyclohexene, and two monoterpenes, (‒)-limonene and (‒)-α-pinene, using two oxidants, aqueous 30% HO or -butyl hydroperoxide (TBHP) in decane, has been studied with catalytic amounts of all complexes. Finally, biological cytotoxicity studies have also been performed with these oxidovanadium(V) compounds for comparison with -dioxidomolybdenum(VI) Schiff base complexes with the same chiral ligands, as well as to determine the cytoprotection against the oxidative damage caused by 30% HO in the HT-22 hippocampal neuronal cells in the range of their 10-100 μM concentration.

摘要

氧化钒(V)配合物, 和 ,与手性四齿席夫碱,它们是(-)-3-氨基-1,2-丙二醇或(+)-3-氨基-1,2-丙二醇与水杨醛衍生物的单缩合产物,已经被合成。不同的光谱方法,即 H 和 V NMR、IR、UV-Vis 和圆二色性,以及元素分析,已被用于其详细的表征。此外,使用两种氧化剂,水相 30%HO 或叔丁基过氧化氢(TBHP)在癸烷中,研究了所有配合物催化量下对苯乙烯、环己烯和两种单萜,(-)-柠檬烯和(-)-α-蒎烯的环氧化作用。最后,还对这些氧化钒(V)化合物进行了生物细胞毒性研究,以与具有相同手性配体的-二氧代钼(VI)席夫碱配合物进行比较,并确定其对 HT-22 海马神经元细胞中 30%HO 引起的氧化损伤的细胞保护作用,范围在其 10-100 μM 浓度内。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4b2b/11084397/fc58ba313354/ijms-25-05010-g001.jpg

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