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

[Display omitted] 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 e...

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Published inMendeleev communications Vol. 32; no. 6; pp. 747 - 749
Main Authors Barkhatova, Darina, Zhukovsky, Daniil, Heim, Christopher, Maiwald, Samuel, Hartmann, Marcus D., Krasavin, Mikhail
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.11.2022
Subjects
2-aminoglutarimide
Cereblon
E3 ubiquitin ligase
immunomodulatory drugs
isocyanides
oxo acids
Ugi reaction
oxo acids
isocyanides
Cereblon
Ugi reaction
E3 ubiquitin ligase
2-aminoglutarimide
immunomodulatory drugs
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Summary:[Display omitted] 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.
ISSN:0959-9436
DOI:10.1016/j.mencom.2022.11.013