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; Xiaoyun Lu; Alberto Massarotti; Antonio Caldarelli; Elisa Ciraolo; Gian Cesare Tron; Emilio Hirsch; Giovanni Sorba; Tracey Pirali

doi:10.1039/c1ob05336a

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, Xiaoyun Lu, Alberto Massarotti, Antonio Caldarelli, Elisa Ciraolo, Gian Cesare Tron, Emilio Hirsch, Giovanni Sorba, Tracey Pirali

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

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.

Lingua originale	Inglese
pagine (da-a)	4144-4149
Numero di pagine	6
Rivista	Organic and Biomolecular Chemistry
Volume	9
Numero di pubblicazione	11
DOI	https://doi.org/10.1039/c1ob05336a
Stato di pubblicazione	Pubblicato - 7 giu 2011

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Guasconi, M., Lu, X., Massarotti, A., Caldarelli, A., Ciraolo, E., Tron, G. C., Hirsch, E., Sorba, G., & Pirali, T. (2011). Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors. Organic and Biomolecular Chemistry, 9(11), 4144-4149. https://doi.org/10.1039/c1ob05336a

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

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.",

author = "Margherita Guasconi and Xiaoyun Lu and Alberto Massarotti and Antonio Caldarelli and Elisa Ciraolo and Tron, {Gian Cesare} and Emilio Hirsch and Giovanni Sorba and Tracey Pirali",

year = "2011",

month = jun,

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doi = "10.1039/c1ob05336a",

language = "English",

volume = "9",

pages = "4144--4149",

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Guasconi, M, Lu, X, Massarotti, A, Caldarelli, A, Ciraolo, E, Tron, GC, Hirsch, E, Sorba, G & Pirali, T 2011, 'Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors', Organic and Biomolecular Chemistry, vol. 9, n. 11, pagg. 4144-4149. https://doi.org/10.1039/c1ob05336a

Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors. / Guasconi, Margherita; Lu, Xiaoyun; Massarotti, Alberto et al.
In: Organic and Biomolecular Chemistry, Vol. 9, N. 11, 07.06.2011, pag. 4144-4149.

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

TY - JOUR

T1 - Groebke multicomponent reaction and subsequent nucleophilic aromatic substitution for a convenient synthesis of 3,8-diaminoimidazo[1,2-a]pyrazines as potential kinase inhibitors

AU - Guasconi, Margherita

AU - Lu, Xiaoyun

AU - Massarotti, Alberto

AU - Caldarelli, Antonio

AU - Ciraolo, Elisa

AU - Tron, Gian Cesare

AU - Hirsch, Emilio

AU - Sorba, Giovanni

AU - Pirali, Tracey

PY - 2011/6/7

Y1 - 2011/6/7

N2 - 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.

AB - 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.

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U2 - 10.1039/c1ob05336a

DO - 10.1039/c1ob05336a

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

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

Abstract

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