Synthesis of novel steroid-peptoid hybrid macrocycles by multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs).
Two new groups of cholane-peptoid hybrid macrocycles were produced by implementing novel combinations of the MiB methodology. Steroid-based hybrid macrolactams including heterocycle and aryl moieties were obtained by utilizing cholanic dicarboxylic acids and diamines in a bidirectional double Ugi-Four-Component (Ugi-4CR) based macrocyclization protocol. Alternatively, N-substituted cyclocholamides were produced from a cholanic pseudo-amino acid by an Ugi-4CR-based cyclooligomerization approach. Both types of macrocycles are steroid-peptoid hybrid macrocycles containing exocyclic peptidic chains. These novel frameworks are a result of the use of bile acids bifunctionalized with carboxylic and amino functionalities as bifunctional building blocks of the Ugi-MiB approach.
Rivera
Daniel G
DG
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle/Saale, Germany.
Wessjohann
Ludger A
LA
D000075202:Contraindications; D003500:Cyclization; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
D047029:Lactams, Macrocyclic; D034444:Peptoids; D013256:Steroids