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Updated: Mar 7, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Comparative Study of the Synthesis and Structural and Physicochemical Properties of Diketopiperazines vs
Pierre Regenass1, Damien Bosc1, Stéphanie Riché1
1Laboratoire d'Innovation Thérapeutique, LabEx MEDALIS, Faculté de Pharmacie, UMR7200 CNRS/Université de Strasbourg , 74 route du Rhin, 67412 Illkirch, France.
Abstract:
Aza-diketopiperazines (aza-DKPs) represent an underprivileged motif obtained by scaffold hopping of 2,5-diketopiperazines (2,5-DKPs). Herein, we compare the synthesis and the structural and physicochemical properties of aza-DKP 4 vs 2,5-DKP 7. Thus, X-ray and 1H NMR studies show that aza-DKP 4 is a rigid and nonflat scaffold like the 2,5-DKP 7. Moreover, the replacement of one Cα-stereogenic center by a nitrogen atom results in a significant improvement of both the water solubility and the microsomal stability.
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