Solid-Phase Synthesis of 4-methylcarboxy-1,4-benzodiazepine-2,5-diones

Pascal Verdié (1) , Gilles Subra (1) , Marie-Christine Averlant-Petit (2) , Muriel Amblard (1) , Jean Martinez (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 LCPM - Laboratoire de Chimie Physique Macromoléculaire

A solid-phase synthesis of 1,4-benzodiazepinone-2,5-diones is described. This new route can afford benzodiazepinone bearing a N-urethane-protected amine and a carboxylic acid function. This kind of building block is valuable as a dipeptide mimic or beta-turn mimetic, and it can be introduced in place of any amino acid in peptide synthesis. Using an "analytical probe" strategy, we optimized the synthesis of a model compound on SynPhase Lanterns. Therefore, the efficiency of several linkers was investigated

Domaines: Chimie organique

Pascal Verdié, Gilles Subra, Marie-Christine Averlant-Petit, Muriel Amblard, Jean Martinez. Solid-Phase Synthesis of 4-methylcarboxy-1,4-benzodiazepine-2,5-diones. Journal of Combinatorial Chemistry, 2008, 10 (6), pp.869-874. ⟨10.1021/cc800085d⟩. ⟨hal-00411034⟩