Issue 11, 2011
From the journal:

Organic & Biomolecular Chemistry

Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors†

Margherita Guasconi,‡a   Xiaoyun Lu,‡bc   Alberto Massarotti,a   Antonio Caldarelli,a   Elisa Ciraolo,b   Gian Cesare Tron,a   Emilio Hirsch,b   Giovanni Sorbaa  and  Tracey Pirali*a  

* Corresponding authors

a DiSCAFF, Università degli Studi del Piemonte Orientale, via Bovio 6, Novara, Italy
E-mail: tracey.pirali@pharm.unipmn.it
Fax: (+39)0321375821
Tel: (+39)0321375853

b Molecular Biotechnology Center, Università degli Studi di Torino, Torino, Italy

c Department of Biological Science and Bioengineering, Key Laboratory of Biomedical Information Engineering of Ministry of Education, School of Life Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, P. R. China

Abstract

In a program aimed at discovering novel protein kinase inhibitors, a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines has been developed exploiting the isocyanide-based multicomponent Blackburn reaction, followed by a nucleophilic aromatic substitution with ammonia or primary and secondary amines. The potential of the reported scaffold is strengthened by the inhibition of STAT5-dependent transcription displayed by four of the synthesized compounds.

Graphical abstract: Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors

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Article information

DOI
https://doi.org/10.1039/C1OB05336A
Article type
Paper
Submitted
25 Jan 2011
Accepted
10 Mar 2011
First published
10 Mar 2011

Org. Biomol. Chem., 2011,9, 4144-4149

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Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors

M. Guasconi, X. Lu, A. Massarotti, A. Caldarelli, E. Ciraolo, G. C. Tron, E. Hirsch, G. Sorba and T. Pirali, Org. Biomol. Chem., 2011, 9, 4144 DOI: 10.1039/C1OB05336A

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