Multicomponent synthesis of dihydrobenzoxazepinones, bearing four diversity points, as potential alpha-helix mimics

作者：Banfi Luca^*; Basso Andrea; Cerulli Valentina; Guanti Giuseppe; Lecinska Paulina; Monfardini Ilaria; Riva Renata

来源：Molecular Diversity, 2010, 14(3): 425-442.

DOI：10.1007/s11030-009-9210-4

• Ugi reaction
• Multicomponent reactions
• Mitsunobu reaction
• Alpha-helix mimics

A very short convergent synthesis of dihydrobenzoxazepinones, bearing four diverse diversity points, based on coupling the Ugi reaction with a Mitsunobu cyclization, was developed. These compounds are potential alpha-helix mimics, where three of the four appendages are expected to imitate the residues in i, i + 4 and i + 7 positions. A library of 22 compounds bearing lipophilic substituents, designed to interact with the hydrophobic cleft of anti-apoptotic protein Bcl-xL, was synthesized. Preliminary biochemical tests, based on competitive binding, have already been carried out.

• 出版日期2010-8