Jump to main content
Jump to site search

Issue 20, 2018
Previous Article Next Article

Chemo-enzymatic synthesis of (E)-2,3-diaryl-5-styryl-trans-2,3-dihydrobenzofuran-based scaffolds and their in vitro and in silico evaluation as a novel sub-family of potential allosteric modulators of the 90 kDa heat shock protein (Hsp90)

Author affiliations

Abstract

Herein we propose a facile, versatile and selective chemo-enzymatic synthesis of substituted (E)-2,3-diaryl-5-styryl-trans-2,3-dihydrobenzofurans based on the exploitation of the laccase-mediated oxidative (homo)coupling of (E)-4-styrylphenols. Thanks to this novel synthetic strategy, a library of benzofuran-based potential allosteric activators of the Heat shock protein 90 (Hsp90) was easily prepared. Moreover, considering their structural analogies to previously reported allosteric modulators, the sixteen new compounds synthesized in this work were tested in vitro for their potential stimulatory action on the ATPase activity of the molecular chaperone Hsp90. Combining experimental and computational results, we propose a mechanism of action for these compounds, and expand the structure–activity relationship (SAR) information available for benzofuran-based Hsp90 activators.

Graphical abstract: Chemo-enzymatic synthesis of (E)-2,3-diaryl-5-styryl-trans-2,3-dihydrobenzofuran-based scaffolds and their in vitro and in silico evaluation as a novel sub-family of potential allosteric modulators of the 90 kDa heat shock protein (Hsp90)

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 Mar 2018, accepted on 27 Apr 2018 and first published on 02 May 2018


Article type: Paper
DOI: 10.1039/C8OB00644J
Org. Biomol. Chem., 2018,16, 3741-3753

  •   Request permissions

    Chemo-enzymatic synthesis of (E)-2,3-diaryl-5-styryl-trans-2,3-dihydrobenzofuran-based scaffolds and their in vitro and in silico evaluation as a novel sub-family of potential allosteric modulators of the 90 kDa heat shock protein (Hsp90)

    I. Bassanini, I. D'Annessa, M. Costa, D. Monti, G. Colombo and S. Riva, Org. Biomol. Chem., 2018, 16, 3741
    DOI: 10.1039/C8OB00644J

Search articles by author

Spotlight

Advertisements