Synthesis of Benzoquinone Ansamycin‐Inspired Macrocyclic Lactams from Shikimic Acid. Issue 18 (2nd April 2013)

• Record Type: Journal Article
• Authors: Jeso, Valer; Iqbal, Sarah; Hernandez, Pamela; Cameron, Michael D.; Park, HaJeung; LoGrasso, Philip V.; Micalizio, Glenn C.
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 18(2013)
• Page Start: 4800
• Page End: 4804
• Publication Date: 2013-04-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201301323
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>One is not like the other</bold>: The title approach proceeds by stepwise coupling of three relatively simple substrates. Three natural product‐inspired agents are described, one of which has natural product‐like toxicity for HeLa and MCF7 cells. It is isoform‐selective, thus targeting Hsp90α/β over Grp94, and adopts a conformation similar to that of geldanamycin when complexed with Hsp90.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg1xpszbgk" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>