Comparative Study of the Synthesis and Structural and Physicochemical Properties of Diketopiperazines vs Aza-diketopiperazines | Zendy

Pierre Regenass | Zendy; Damien Bosc | Zendy; Stéphanie Riché | Zendy; Patrick Gizzi | Zendy; Marcel Hibert | Zendy; Lydia Karmazin | Zendy; A. Ganesan | Zendy; Dominique Bonnet | Zendy

Open Access

Comparative Study of the Synthesis and Structural and Physicochemical Properties of Diketopiperazines vs Aza-diketopiperazines

Author(s) -

Pierre Regenass,

Damien Bosc,

Stéphanie Riché,

Patrick Gizzi,

Marcel Hibert,

Lydia Karmazin,

A. Ganesan,

Dominique Bonnet

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b02895

Subject(s) - diketopiperazines , solubility , nitrogen atom , chemistry , scaffold , stereochemistry , organic chemistry , group (periodic table) , medicine , biomedical engineering

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 1 H NMR studies show that aza-DKP 4 is a rigid and nonflat scaffold like the 2,5-DKP 7. Moreover, the replacement of one C α -stereogenic center by a nitrogen atom results in a significant improvement of both the water solubility and the microsomal stability.

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