Synthesis 2016; 48(22): 3907-3916
DOI: 10.1055/s-0035-1562497
paper
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • Giordano Lesma

    a   Dipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
  • Andrea Luraghi

    a   Dipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
  • Giulia Rainoldi

    a   Dipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
  • Elena Mattiuzzo

    b   Dipartimento di salute della Donna e del Bambino, Università di Padova, Via Giustiniani 3, Padova, 35128, Italy   eMail: alessandra.silvani@unimi.it
  • Roberta Bortolozzi

    b   Dipartimento di salute della Donna e del Bambino, Università di Padova, Via Giustiniani 3, Padova, 35128, Italy   eMail: alessandra.silvani@unimi.it
  • Giampietro Viola

    b   Dipartimento di salute della Donna e del Bambino, Università di Padova, Via Giustiniani 3, Padova, 35128, Italy   eMail: alessandra.silvani@unimi.it
  • Alessandra Silvani*

    a   Dipartimento di Chimica, Università di Milano, via Golgi 19, Milano, 20133, Italy
Weitere Informationen

Publikationsverlauf

Received: 16. März 2016

Accepted after revision: 17. Mai 2016

Publikationsdatum:
01. Juli 2016 (online)


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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.

Supporting Information