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

Giordano Lesma; Andrea Luraghi; Giulia Rainoldi; Elena Mattiuzzo; Roberta Bortolozzi; Giampietro Viola; Alessandra Silvani

doi:10.1055/s-0035-1562497

Synthesis, Table of Contents

Synthesis 2016; 48(22): 3907-3916
DOI: 10.1055/s-0035-1562497

paper

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

Authors

Giordano Lesma

^aDipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
Andrea Luraghi

^aDipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
Giulia Rainoldi

^aDipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
Elena Mattiuzzo

^bDipartimento di salute della Donna e del Bambino, Università di Padova, Via Giustiniani 3, Padova, 35128, Italy Email: alessandra.silvani@unimi.it
Roberta Bortolozzi

^bDipartimento di salute della Donna e del Bambino, Università di Padova, Via Giustiniani 3, Padova, 35128, Italy Email: alessandra.silvani@unimi.it
Giampietro Viola

^bDipartimento di salute della Donna e del Bambino, Università di Padova, Via Giustiniani 3, Padova, 35128, Italy Email: alessandra.silvani@unimi.it
Alessandra Silvani*

^aDipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy

Abstract

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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.

Key words

steroids - peptide-steroid conjugates - multicomponent reactions - Ugi reaction - multidrug resistance

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References

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