This paper describes the enantioselective synthesis of analogues of sapinofuranones A and B, namely 5-substitutes dihydro- and 5H-furan-ones, and their in vitro growth inhibitory activity against six cancer cell lines in comparison with fungal furanones such as diplofuranone A, diplobifuranylones A and B, as well as (S,S)-enantiomer of sapinofuranone B. The compounds under study displayed weak if any in vitro growth inhibitory activity against the analysed cancer cell lines. However, it seems that among dihydro- and 5H-furan-ones bearing a 1-hydroxypentyl side chain, the stereochemistry of the furanone ring and that of hydroxylated methine could modify the in vitro growth activity of these compounds. The natural furanones that showed a different unsaturated chain at C-4 or rearranged into a dihydrofuran ring appeared to be inactive in terms of growth inhibitory activity, e.g. displaying growth inhibitory concentration at 50% (GI50) > 100 μM in all six cancer cell lines analysed.

Natural and synthetic furanones with anticancer activity / Cimmino, A.; Scafato, P; Mathieu, V.; Ingels, A.; D'Amico, W.; Pisani L, .; Maddau, Lucia; Superchi, S.; Kiss, R.; Evidente, A.. - In: NATURAL PRODUCT COMMUNICATIONS. - ISSN 1555-9475. - 11:10(2016), pp. 1471-1474.

Natural and synthetic furanones with anticancer activity

MADDAU, Lucia;
2016

Abstract

This paper describes the enantioselective synthesis of analogues of sapinofuranones A and B, namely 5-substitutes dihydro- and 5H-furan-ones, and their in vitro growth inhibitory activity against six cancer cell lines in comparison with fungal furanones such as diplofuranone A, diplobifuranylones A and B, as well as (S,S)-enantiomer of sapinofuranone B. The compounds under study displayed weak if any in vitro growth inhibitory activity against the analysed cancer cell lines. However, it seems that among dihydro- and 5H-furan-ones bearing a 1-hydroxypentyl side chain, the stereochemistry of the furanone ring and that of hydroxylated methine could modify the in vitro growth activity of these compounds. The natural furanones that showed a different unsaturated chain at C-4 or rearranged into a dihydrofuran ring appeared to be inactive in terms of growth inhibitory activity, e.g. displaying growth inhibitory concentration at 50% (GI50) > 100 μM in all six cancer cell lines analysed.
Natural and synthetic furanones with anticancer activity / Cimmino, A.; Scafato, P; Mathieu, V.; Ingels, A.; D'Amico, W.; Pisani L, .; Maddau, Lucia; Superchi, S.; Kiss, R.; Evidente, A.. - In: NATURAL PRODUCT COMMUNICATIONS. - ISSN 1555-9475. - 11:10(2016), pp. 1471-1474.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/174726
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 2
social impact