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, P. Mátyus, S. Antus, T. Kurtán

Research output: Article

5 Citations (Scopus)

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
JournalChirality
DOIs
Publication statusAccepted/In press - jan. 1 2018

Fingerprint

High performance liquid chromatography
Dichroism
Circular Dichroism
Density functional theory
High Pressure Liquid Chromatography
Derivatives
Stereoisomerism
Enantiomers
Cyclization
Spiro Compounds
Acetylcholinesterase
Hydrides
Oxygen
Neuroblastoma
Glucose
quinoline
1,3-cyclohexanedione

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., ... Kurtán, T. (Accepted/In press). HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives. Chirality. https://doi.org/10.1002/chir.22969

HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives. / Tóth, László; Mándi, Attila; Váradi, Dániel; Kovács, Tibor; Szabados, Anna; Kiss-Szikszai, Attila; Gong, Qi; Zhang, Haiyan; Mátyus, P.; Antus, S.; Kurtán, T.

In: Chirality, 01.01.2018.

Research output: Article

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. https://doi.org/10.1002/chir.22969
Tóth L, Mándi A, Váradi D, Kovács T, Szabados A, Kiss-Szikszai A et al. HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives. Chirality. 2018 jan. 1. https://doi.org/10.1002/chir.22969
Tóth, László ; Mándi, Attila ; Váradi, Dániel ; Kovács, Tibor ; Szabados, Anna ; Kiss-Szikszai, Attila ; Gong, Qi ; Zhang, Haiyan ; Mátyus, P. ; Antus, S. ; Kurtán, T. / HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives. In: Chirality. 2018.
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AU - Szabados, Anna

AU - Kiss-Szikszai, Attila

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AU - Antus, S.

AU - Kurtán, T.

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AB - 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.

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