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      Synthesis of ether analogues derived from HUN-7293 and evaluation as inhibitors of VCAM-1 expression.

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          Abstract

          The cyclic depsipeptide HUN-7293 (1) and its D-lactate analogue 2 are highly potent inhibitors of inducible cell adhesion molecule expression. We report the synthesis of ether analogues varying in stereochemistry and side chain at the former hydroxyl acid position by employing a 'cut and paste chemistry' methodology starting from 1. As an additional fruit of this synthetic effort, a cyclodepsipeptide featuring a tertiary amine instead of a tertiary amide between PrLEU and MALA was obtained. Results on the inhibitory profile of these compounds in assays of VCAM-1 and ICAM-1 protein expression are discussed.

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          Author and article information

          Journal
          Bioorg. Med. Chem. Lett.
          Bioorganic & medicinal chemistry letters
          Elsevier BV
          0960-894X
          0960-894X
          Oct 04 2004
          : 14
          : 19
          Affiliations
          [1 ] Novartis Institutes for BioMedical Research GDC, Brunner Strasse 59, A-1235 Vienna, Austria. erwin.schreiner@pharma.novartis.com
          Article
          S0960-894X(04)00901-1
          10.1016/j.bmcl.2004.07.012
          15341969
          ea12c0a0-45d5-4fd9-9f05-d58ec6350f7f
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