Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases

Gyte Vilkauskaite; Patricia Schaaf; Algirdas Sackus; Vladimir Krystof; Wolfgang Holzer

doi:10.3998/ark.5550190.p008.188

Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases

Gyte Vilkauskaite, Patricia Schaaf, Algirdas Sackus, Vladimir Krystof, Wolfgang Holzer

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

A synthetic route towards 3-(2-pyridyl)-6-(hetero)aryl-1H-pyrazolo[4,3-c]pyridines is described.The key step consists of a microwave-assisted multi-component reaction, including a Sonogashira type cross-coupling of appropriate 5-chloropyrazole-4-carbaldehydes with alkynyl-(hetero)arenes followed by pyridine ring formation of the coupling products in the presence oftert-butylamine, directly affording the title compounds. A congener without substituent at N-1was accessed via cleavage of a tert-butyl protecting group. Detailed NMR spectroscopic studies (1H, 13C and 15N) were undertaken with the obtained compounds. Selected representatives were
evaluated for their potential as inhibitors of protein kinases.

Original language	English
Pages (from-to)	135-149
Number of pages	15
Journal	ARKIVOC
Volume	2014
Issue number	2
DOIs	https://doi.org/10.3998/ark.5550190.p008.188
Publication status	Published - 2014

Austrian Fields of Science 2012

104015 Organic chemistry
301207 Pharmaceutical chemistry
301206 Pharmacology

Keywords

15N NMR spectroscopy
Cyclin-dependent kinase (CDK) inhibitors
Fused pyrazoles, pyridines
Multi-component reactions
Pyrazolones
Sonogashira reaction

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10.3998/ark.5550190.p008.188Licence: CC BY-NC 3.0

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title = "Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases",

abstract = "A synthetic route towards 3-(2-pyridyl)-6-(hetero)aryl-1H-pyrazolo[4,3-c]pyridines is described.The key step consists of a microwave-assisted multi-component reaction, including a Sonogashira type cross-coupling of appropriate 5-chloropyrazole-4-carbaldehydes with alkynyl-(hetero)arenes followed by pyridine ring formation of the coupling products in the presence oftert-butylamine, directly affording the title compounds. A congener without substituent at N-1was accessed via cleavage of a tert-butyl protecting group. Detailed NMR spectroscopic studies (1H, 13C and 15N) were undertaken with the obtained compounds. Selected representatives wereevaluated for their potential as inhibitors of protein kinases. ",

keywords = "15N NMR spectroscopy, Cyclin-dependent kinase (CDK) inhibitors, Fused pyrazoles, pyridines, Multi-component reactions, Pyrazolones, Sonogashira reaction",

author = "Gyte Vilkauskaite and Patricia Schaaf and Algirdas Sackus and Vladimir Krystof and Wolfgang Holzer",

year = "2014",

doi = "10.3998/ark.5550190.p008.188",

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AU - Vilkauskaite, Gyte

AU - Schaaf, Patricia

AU - Sackus, Algirdas

AU - Krystof, Vladimir

AU - Holzer, Wolfgang

PY - 2014

Y1 - 2014

N2 - A synthetic route towards 3-(2-pyridyl)-6-(hetero)aryl-1H-pyrazolo[4,3-c]pyridines is described.The key step consists of a microwave-assisted multi-component reaction, including a Sonogashira type cross-coupling of appropriate 5-chloropyrazole-4-carbaldehydes with alkynyl-(hetero)arenes followed by pyridine ring formation of the coupling products in the presence oftert-butylamine, directly affording the title compounds. A congener without substituent at N-1was accessed via cleavage of a tert-butyl protecting group. Detailed NMR spectroscopic studies (1H, 13C and 15N) were undertaken with the obtained compounds. Selected representatives wereevaluated for their potential as inhibitors of protein kinases.

AB - A synthetic route towards 3-(2-pyridyl)-6-(hetero)aryl-1H-pyrazolo[4,3-c]pyridines is described.The key step consists of a microwave-assisted multi-component reaction, including a Sonogashira type cross-coupling of appropriate 5-chloropyrazole-4-carbaldehydes with alkynyl-(hetero)arenes followed by pyridine ring formation of the coupling products in the presence oftert-butylamine, directly affording the title compounds. A congener without substituent at N-1was accessed via cleavage of a tert-butyl protecting group. Detailed NMR spectroscopic studies (1H, 13C and 15N) were undertaken with the obtained compounds. Selected representatives wereevaluated for their potential as inhibitors of protein kinases.

KW - 15N NMR spectroscopy

KW - Cyclin-dependent kinase (CDK) inhibitors

KW - Fused pyrazoles, pyridines

KW - Multi-component reactions

KW - Pyrazolones

KW - Sonogashira reaction

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U2 - 10.3998/ark.5550190.p008.188

DO - 10.3998/ark.5550190.p008.188

M3 - Article

SN - 1551-7004

VL - 2014

SP - 135

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JO - ARKIVOC

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IS - 2

ER -

Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases

Abstract

Austrian Fields of Science 2012

Keywords

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