HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives.
László TóthAttila MándiDániel VáradiTibor KovácsAnna SzabadosAttila Kiss-SzikszaiQi GongHaiyan ZhangPéter MátyusSándor AntusTibor KurtánPublished in: Chirality (2018)
Synthesis of racemic hexahydropyrrolo[1,2-a]quinoline derivatives (1-8) was performed by utilizing the Knoevenagel-[1,5]-hydride shift-cyclization domino reaction. Separation of the enantiomers of the chiral products (1-8) was carried out by chiral high-performance liquid chromatography, and online high-performance liquid chromatography-electronic circular dichroism (ECD) spectra were recorded to elucidate the absolute configuration by comparing the experimental and time-dependent density functional theory-ECD spectra obtained at various theoretical levels. For 1 of the products, the time-dependent density functional theory-ECD calculations allowed determining both the relative and the absolute configuration by distinguishing the 4 stereoisomers. One of the compounds with spiro 1,3-cyclohexanedione moiety (7) possessed moderate acetylcholinesterase inhibitory activity, while 3 showed neuroprotective activity in oxygen-glucose deprivation-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.
Keyphrases
- density functional theory
- high performance liquid chromatography
- tandem mass spectrometry
- mass spectrometry
- simultaneous determination
- molecular dynamics
- solid phase extraction
- capillary electrophoresis
- liquid chromatography
- ms ms
- induced apoptosis
- endothelial cells
- molecular docking
- ionic liquid
- high intensity
- cell cycle arrest
- high resolution
- endoplasmic reticulum stress
- metabolic syndrome
- blood glucose
- oxidative stress
- signaling pathway
- brain injury
- induced pluripotent stem cells
- blood pressure
- cell death