title: Comparative Study of the Synthesis and Structural and Physicochemical Properties of Diketopiperazines vs Aza-diketopiperazines.
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 and1H 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.
authors.affiliation: Laboratoire d'Innovation Thérapeutique, LabEx MEDALIS, Faculté de Pharmacie, UMR7200 CNRS/Université de Strasbourg , 74 route du Rhin, 67412 Illkirch, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Regenass
authors.affiliation: Laboratoire d'Innovation Thérapeutique, LabEx MEDALIS, Faculté de Pharmacie, UMR7200 CNRS/Université de Strasbourg , 74 route du Rhin, 67412 Illkirch, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Bosc
authors.affiliation: Laboratoire d'Innovation Thérapeutique, LabEx MEDALIS, Faculté de Pharmacie, UMR7200 CNRS/Université de Strasbourg , 74 route du Rhin, 67412 Illkirch, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Riché
authors.affiliation: Université de Strasbourg, CNRS , Plateforme de Chimie Biologie Intégrative (PCBIS), UMS3286 and LabEx MEDALIS 6700 Strasbourg, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Gizzi
authors.affiliation: Laboratoire d'Innovation Thérapeutique, LabEx MEDALIS, Faculté de Pharmacie, UMR7200 CNRS/Université de Strasbourg , 74 route du Rhin, 67412 Illkirch, France.
authors.forename: Marcel
authors.initials: M
authors.lastname: Hibert
authors.affiliation: Service de Cristallographie, Institut de Chimie de Strasbourg , BP 296/R8, 67008 Strasbourg, France.
authors.forename: Lydia
authors.initials: L
authors.lastname: Karmazin
authors.affiliation: School of Pharmacy, University of East Anglia , Norwich Research Park, Norwich NR4 7TJ, U.K.
authors.forename: A
authors.initials: A
authors.lastname: Ganesan
authors.affiliation: Laboratoire d'Innovation Thérapeutique, LabEx MEDALIS, Faculté de Pharmacie, UMR7200 CNRS/Université de Strasbourg , 74 route du Rhin, 67412 Illkirch, France.
authors.forename: Dominique
authors.identifier: 0000-0002-8252-9199
authors.initials: D
authors.lastname: Bonnet
mesh_terms: D000818:Animals; D056148:Chromatography, Reverse-Phase; D018360:Crystallography, X-Ray; D051379:Mice; D008862:Microsomes, Liver / Q000187:drug effects; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013057:Spectrum Analysis
chemical_list: D010879:Piperazines