Syntheses of novel 2,3-diaryl-substituted 5-cyano-4-azaindoles exhibiting c-Met inhibition activity

Koolman, Hannes F.; Heinrich, Timo; Böttcher, Henning; Rautenberg, Wilfried; Reggelin, Michael

doi:10.1016/j.bmcl.2009.02.069

Cited by 30 publications

(10 citation statements)

References 18 publications

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“…Inspired by these discoveries, H. Koolman et al executed a complementary route employing Larock methodology to synthesize a tyrosine kinase inhibitor, a 4-azaindole core attached to a diaryl substitution in the C-2 and C-3 position of 27 (yields from 48 to 66%, over two steps). These products were not isolated since they were a part of an extensive synthesis ( Scheme 11 ) [ 17 ].…”

Section: Metal-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

2018

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Azaindoles are rare in nature but extremely attractive for drug discovery programs. Azaindoles can be obtained by diverse methods, including those involving metal-catalyzed reactions. This important core has been fascinating the scientific community due to their challenging synthesis and relevant bioactivity. This paper highlights the diverse synthetic methodologies developed to date involving metal-catalyzed reaction to attain azaindoles and its functionalization.

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Section: Metal-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

2018

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“…In a variety of cancer types c-Met is overexpressed and leads to high proliferation scattering, invasiveness and metastasis development. ATP competitive c-Met kinase inhibitors such as compound 59 have been reported in the literature [61]. A Sonogashira reaction of 4-pyridinylethyne ( 57 ) with iodopyridine 56 afforded the 5-cyano-2-(4-pyridinyl)-4-azaindole derivative 58 after cyclization with potassium tert -butoxide (Scheme 11).…”

Section: C-met Kinase Inhibitorsmentioning

confidence: 99%

The Azaindole Framework in the Design of Kinase Inhibitors

et al. 2014

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This review article illustrates the growing use of azaindole derivatives as kinase inhibitors and their contribution to drug discovery and innovation. The different protein kinases which have served as targets and the known molecules which have emerged from medicinal chemistry and Fragment-Based Drug Discovery (FBDD) programs are presented. The various synthetic routes used to access these compounds and the chemical pathways leading to their synthesis are also discussed. An analysis of their mode of binding based on X-ray crystallography data gives structural insights for the design of more potent and selective inhibitors.

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“…Later, after the synthesis of 2,3‐diaryl‐substituted 5‐cyano‐4‐azaindoles, reported by Koolman et al to afford c‐Met inhibition activity, copper‐free Sonogashira‐type coupling between 3‐amino‐6‐cyano‐2‐iodopyridine ( 47 ) and 4‐ethynylpyridine ( 48 ) was accomplished, affording product 49 in 66 % yield with use of Cs 2 CO 3 as base and Pd(dppf)Cl 2 in THF at 50 °C (Scheme ) 53. The Cacchi procedure48a was also attempted by the authors in the hope of obtaining the desired 5‐cyano‐substituted azaindoles.…”

Section: C–c Cross‐coupling Reactionsmentioning

confidence: 99%

Metal‐Catalyzed Cross‐Coupling Reactions of Aminopyridines

2015

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The aminopyridines are key building blocks in the synthesis of bioactive heterocyclic compounds such as azaindoles and imidazopyridines. The role of metal-catalyzed methods in aminopyridine functionalization, in particular the catalytic systems used, reaction conditions and the influence of aminopyridine substituents on the reaction outcome, is outlined. The review covers different metal-catalyzed reactions developed for C-C and C-N bond formation. One-pot and multicomponent reactions directed towards aminopyridine-

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Syntheses of novel 2,3-diaryl-substituted 5-cyano-4-azaindoles exhibiting c-Met inhibition activity

Cited by 30 publications

References 18 publications

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

The Azaindole Framework in the Design of Kinase Inhibitors

Metal‐Catalyzed Cross‐Coupling Reactions of Aminopyridines

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