Multicomponent Approach to Bioactive Peptide–Ecdysteroid Conjugates: Creating Diversity at C6 by Means of the Ugi Reaction

2016/07/01 by Alessandra Silvani, Giordano Lesma, Andrea Luraghi +4 · 12 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Materials Science · Neuroscience · #Amino acid #Biochemistry #Chemistry #Combinatorial chemistry #Conjugate #Ecdysone #Ecdysteroid #Hormone #Isocyanide #Marine Sponges and Natural Products #Neurobiology and Insect Physiology Research #Organic chemistry #Peptide #Photochromic and Fluorescence Chemistry #Reactivity (psychology) #Ugi reaction

paper · doi:10.1055/s-0035-1562497

published in Synthesis 48(22), 3907-3916 (Thieme Medical Publishers (Germany))

openalex publication_date 2016/07/01 · openalex created_date 2016/07/22 · openalex updated_date 2026/08/04

Abstract

An efficient multicomponent protocol has been developed to access two different kinds of peptide–ecdysteroid conjugates. The approach exploits the reactivity of the 6-keto-7-ene group of 20-OH-ecdysone, allowing the unprecedented preparation of 6-amino and 6-isocyanide derivatives. The ecdysteroid derivatives were further employed in the Ugi reaction, together with formaldehyde and various structurally diverse carboxylic acids, isocyanides and amines, to afford a small family of potential multidrug-resistance modulators.

Cited by

• Steroid diversification by multicomponent reactions. [europepmc]
• Ecdysteroid Derivatives that Reverse P-Glycoprotein-Mediated Drug Resistance. [europepmc]
• Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions. [europepmc]
• A First Diversity-Oriented N -Maleopimarimido-Isocyanide for Multicomponent Reactions: Synthesis, Application, and In Silico Evaluation. [europepmc]

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