D. Barkhatova, D. Zhukovsky, Ch. Heim, S. Maiwald, M. D. Hartmann, M. Yu. Krasavin, “Synthesis of novel glutarimide derivatives <i>via</i> the Ugi multicomponent reaction: affinity towards the E3 ubiquitin ligase substrate receptor Cereblon”, Mendeleev Commun., 2022, Volume 32, Issue 6,Pages <nobr>747

This article is cited in 1 paper

Communications

Synthesis of novel glutarimide derivatives via the Ugi multicomponent reaction: affinity towards the E3 ubiquitin ligase substrate receptor Cereblon

D. Barkhatova^a, D. Zhukovsky^a, Ch. Heim^bc, S. Maiwald^c, M. D. Hartmann^bc, M. Yu. Krasavin^ad

^a Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^b Interfaculty Institute of Biochemistry, University of Tubingen, Tubingen, Germany
^c Department of Protein Evolution, Max Planck Institute for Biology, Tubingen, Germany
^d Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation

Abstract: The glutarimide moiety, common in many immuno-modulatory drugs, was decorated with lactam and diamide side chains via two variants of the Ugi reaction, namely, with isocyanide, aldehyde and acid or with isocyanide and oxo acid. The resulting diastereomerically pure compounds were evaluated for their affinity towards the E3 ubiquitin ligase substrate receptor Cereblon.

Keywords: 2-aminoglutarimide, Ugi reaction, oxo acids, isocyanides, immunomodulatory drugs, E3 ubiquitin ligase, Cereblon.

Language: English

DOI: 10.1016/j.mencom.2022.11.013

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