HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives

László Tóth, Attila Mándi, Dániel Váradi, Tibor Kovács, Anna Szabados, Attila Kiss-Szikszai, Qi Gong, Haiyan Zhang, Péter Mátyus, Sándor Antus, Tibor Kurtán

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Abstract

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.

Original languageEnglish
Pages (from-to)866-874
Number of pages9
JournalChirality
Volume30
Issue number7
DOIs
Publication statusPublished - Jul 2018

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Keywords

  • C-H activation
  • [1,5]-hydride shift
  • density functional theory
  • relative and absolute configuration

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Tóth, L., Mándi, A., Váradi, D., Kovács, T., Szabados, A., Kiss-Szikszai, A., Gong, Q., Zhang, H., Mátyus, P., Antus, S., & Kurtán, T. (2018). HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives. Chirality, 30(7), 866-874. https://doi.org/10.1002/chir.22969