Synthesis and antiproliferative activity of 6-naphthylpterocarpans

Organic & Biomolecular Chemistry
Ádám SzappanosTibor Kurtán

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.

References

Feb 1, 1996·Journal of Molecular Graphics·W HumphreyK Schulten
Mar 29, 2003·Journal of Natural Products·Jing-Ru WengChun-Nan Lin
Dec 28, 2005·Journal of Natural Products·Tamara L MeragelmanRobert H Shoemaker
Sep 7, 2006·Journal of Computational Chemistry·Stefan Grimme
Sep 4, 2007·Bioorganic & Medicinal Chemistry·Gardenia C G MilitãoEdilberto R Silveira
Dec 7, 2007·Bioorganic & Medicinal Chemistry·Nashira Campos VieiraEdilberto Rocha Silveira
May 13, 2008·European Journal of Medicinal Chemistry·Chaquip D NettoPaulo R R Costa
May 1, 2009·Journal of Agricultural and Food Chemistry·Huiping ZhouLiangli Lucy Yu
Apr 7, 2010·Bioorganic & Medicinal Chemistry·Phi Hung NguyenWon Keun Oh
Aug 10, 2011·Bioorganic & Medicinal Chemistry·Ruth DevakaramNaresh Kumar
Mar 6, 2012·Organic Letters·Thomas J A Graham, Abigail G Doyle
Sep 8, 2012·Organic & Biomolecular Chemistry·Atul GoelGerhard Bringmann
Jun 9, 2016·The Journal of Organic Chemistry·Brian M MullerMarc J Adler
Feb 2, 2017·Beilstein Journal of Organic Chemistry·Viktor IlkeiTibor Kurtán
Feb 12, 2017·European Journal of Medicinal Chemistry·Chelliah SelvamRamasamy Thilagavathi
Feb 22, 2018·Journal of Agricultural and Food Chemistry·Alfonso Alejo-ArmijoElena Ortega-Morente
Aug 25, 2018·Journal of Agricultural and Food Chemistry·C Peter Constabel
Jan 12, 2019·Natural Product Reports·Nawaf Al-Maharik
May 30, 2019·Natural Product Reports·Attila Mándi, Tibor Kurtán

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Citations

Mar 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dóra Szalóki VargánéTibor Kurtán

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Methods Mentioned

BETA
NMR
circular dichroism
column chromatography

Software Mentioned

TDDFT
VMD
Origin
ECD
MMFF
Macromodel
Gaussian

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