2-Amino-3-(phenylsulfanyl)norbornane-2-carboxylate: An appealing scaffold for the design of Rac1-Tiam1 protein-protein interaction inhibitors

Alessandro Ruffoni, Nicola Ferri, Sergio K. Bernini, Chiara Ricci, Alberto Corsini, Irene Maffucci, Francesca Clerici, Alessandro Contini

Research output: Contribution to journalArticlepeer-review

Abstract

The use of the 2-amino-3-(phenylsulfanyl)norbornane-2-carboxylate scaffold has been exploited for the de novo design of potent Rac1 inhibitors acting as modulators of the protein-protein interaction between Rac1 and Tiam1. A series of compounds differing in regio- and stereochemistry has been prepared by way of a multistep synthesis based on cycloaddition reactions and Pd chemistry. Pharmacological analyses showed that all the prepared compounds were active and selective for Rac1, and the most effective compound 13 was capable of inhibiting smooth muscle cell migration the synthesis of this derivative was successfully scaled up to 1 g.

Original languageEnglish
Pages (from-to)2953-2962
Number of pages10
JournalJournal of Medicinal Chemistry
Volume57
Issue number7
DOIs
Publication statusPublished - Apr 10 2014

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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