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Molecules 2008, 13(4), 995-1003; doi:10.3390/molecules13040995
Article

Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1

1,* , 1, 1, 2 and 2
1 Department of Chemistry, University of Düsseldorf, Universitätstr. 1, D-40225 Düsseldorf, Germany 2 Max-Planck Research Unit for Enzymology of Protein Folding, Weinbergweg 22, D-06120 Halle, Germany
* Author to whom correspondence should be addressed.
Received: 3 April 2008 / Revised: 22 April 2007 / Accepted: 23 April 2008 / Published: 29 April 2008
(This article belongs to the Special Issue Spiro Compounds)
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Abstract

The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been madeaccessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclicbenzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 isdescribed. The novel spirocyclic benzofuranones display modest to no inhibition of thehuman peptidyl prolyl cis/trans isomerase Pin1.
Keywords: Ketones; lithiation; cyclization; metathesis; spiroannulation Ketones; lithiation; cyclization; metathesis; spiroannulation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Braun, M.; Hessamian-Alinejad, A.; De Lacroix, B.F.; Alvarez, B.H.; Fischer, G. Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1. Molecules 2008, 13, 995-1003.

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