Synthesis and antiproliferative activity of 6-naphthylpterocarpans

Ádám Szappanos, Attila Mándi, Katalin Gulácsi, Erika Lisztes, Balázs István Tóth, Tamás Bíró, Sándor Antus, Tibor Kurtán

Research output: Article

1 Citation (Scopus)

Abstract

The Heck-oxyarylation of racemic 2-(1-naphthyl)-and 2-(2-naphthyl)-2H-chromene derivatives were carried out resulting diastereoselectively in (6S∗,6aR∗,11aR∗)-6-(1-naphthyl)-and 6-(2-naphthyl)-pterocarpans as major products and bridged (6R∗,12R∗)-6,12-methanodibenzo[d,g][1,3]dioxocine derivatives as minor products. Antiproliferative activity of two 6-naphthylpterocarpans was identified by MTT assay against A2780 and WM35 human cancer cell lines with low micromolar IC50 values. The measured 0.80 and 3.51 μM IC50 values of the (6S∗,6aR∗,11aR∗)-6-(1-naphthyl)pterocarpan derivative with 8,9-methylenedioxy substitution represent the best activities in the pterocarpan family. Enantiomers of the pterocarpan and dioxocine derivatives and their chiral 2-naphthylchroman-4-one and 2-naphthyl-2H-chromene precursors were separated by HPLC using chiral stationary phase. HPLC-ECD spectra were recorded and absolute configuration and low-energy solution conformations were determined by TDDFT-ECD calculations. Characteristic ECD transitions of the separated enantiomers were correlated with their absolute configuration.

Original languageEnglish
Pages (from-to)2148-2162
Number of pages15
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number11
DOIs
Publication statusPublished - márc. 21 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Szappanos, Á., Mándi, A., Gulácsi, K., Lisztes, E., Tóth, B. I., Bíró, T., Antus, S., & Kurtán, T. (2020). Synthesis and antiproliferative activity of 6-naphthylpterocarpans. Organic and Biomolecular Chemistry, 18(11), 2148-2162. https://doi.org/10.1039/d0ob00110d