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Issue 37, 2016
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A step-economical multicomponent synthesis of 3D-shaped aza-diketopiperazines and their drug-like chemical space analysis

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Abstract

A rapid and atom economical multicomponent synthesis of complex aza-diketopiperazines (aza-DKPs) driven by Rh(I)-catalyzed hydroformylation of alkenylsemicarbazides is described. Combined with catalytic amounts of acid and the presence of nucleophilic species, this unprecedented multicomponent reaction (MCR) enabled the formation of six bonds and a controlled stereocenter from simple substrates. The efficacy of the strategy was demonstrated with a series of various allyl-substituted semicarbazides and nucleophiles leading to the preparation of 3D-shaped bicyclic aza-DKPs. Moreover, an analysis of their 3D molecular descriptors and “drug-likeness” properties highlights not only their originality in the chemical space of aza-heterocycles but also their great potential for medicinal chemistry.

Graphical abstract: A step-economical multicomponent synthesis of 3D-shaped aza-diketopiperazines and their drug-like chemical space analysis

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Supplementary files

Article information


Submitted
04 Jul 2016
Accepted
22 Aug 2016
First published
22 Aug 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 8859-8863
Article type
Paper

A step-economical multicomponent synthesis of 3D-shaped aza-diketopiperazines and their drug-like chemical space analysis

P. Regenass, S. Riché, F. Péron, D. Rognan, M. Hibert, N. Girard and D. Bonnet, Org. Biomol. Chem., 2016, 14, 8859
DOI: 10.1039/C6OB01434H

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