1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis

László Tóth, Attila Kiss-Szikszai, Gábor Vasvári, Ferenc Fenyvesi, M. Vecsernyés, P. Mátyus, S. Antus, Attila Mándi, T. Kurtán

Research output: Contribution to journal › Article

Abstract

Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.

Original languageEnglish
Pages (from-to)799-803
Number of pages5
JournalSynlett
Volume30
Issue number7
DOIs
Publication statusPublished - Jan 1 2019

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Benzopyrans
Amination
Enantiomers
Isomerization
Cells
Derivatives

Keywords

  • 1,2-dihydrochromeno[2,3-c]pyrrol-3-one
  • antiproliferative
  • HPLC-ECD
  • isomerization
  • TDDFT-ECD

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives : Synthesis and HPLC-ECD Analysis. / Tóth, László; Kiss-Szikszai, Attila; Vasvári, Gábor; Fenyvesi, Ferenc; Vecsernyés, M.; Mátyus, P.; Antus, S.; Mándi, Attila; Kurtán, T.

In: Synlett, Vol. 30, No. 7, 01.01.2019, p. 799-803.

Research output: Contribution to journal › Article

Tóth, L, Kiss-Szikszai, A, Vasvári, G, Fenyvesi, F, Vecsernyés, M, Mátyus, P, Antus, S, Mándi, A & Kurtán, T 2019, '1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis', Synlett, vol. 30, no. 7, pp. 799-803. https://doi.org/10.1055/s-0037-1612085
Tóth L, Kiss-Szikszai A, Vasvári G, Fenyvesi F, Vecsernyés M, Mátyus P et al. 1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis. Synlett. 2019 Jan 1;30(7):799-803. https://doi.org/10.1055/s-0037-1612085
Tóth, László ; Kiss-Szikszai, Attila ; Vasvári, Gábor ; Fenyvesi, Ferenc ; Vecsernyés, M. ; Mátyus, P. ; Antus, S. ; Mándi, Attila ; Kurtán, T. / 1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives : Synthesis and HPLC-ECD Analysis. In: Synlett. 2019 ; Vol. 30, No. 7. pp. 799-803.
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