Synthesis of highly substituted dibenzo[b,f]azocines and their evaluation as protein kinase inhibitors

Leggy A. Arnold; R. Kiplin Guy

doi:10.1016/j.bmcl.2006.07.078

Synthesis of highly substituted dibenzo[b,f]azocines and their evaluation as protein kinase inhibitors

Leggy A. Arnold, R. Kiplin Guy

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Synthetic routes towards highly substituted eight membered ring heterocycles fused to aryl rings such as the dibenzo[b,f]azocine system are still lacking. Herein, we present a convenient convergent synthetic route towards this heterocyclic class of compounds with possible variations at positions 4, 7, and 11. One member of a library of dibenzo[b,f]azocines with different substituents at position 11 was identified to inhibit protein kinase A activity (IC₅₀ = 122 μM) but not protein kinase C.

Original language	English
Pages (from-to)	5360-5363
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	20
DOIs	https://doi.org/10.1016/j.bmcl.2006.07.078
State	Published - Oct 15 2006

Bibliographical note

Funding Information:
This work was supported by the HHMI Research Resources Program Grant No. 76296-549901, the NIH (R01 No. DK58080), and the Sandler Research Foundation.

Keywords

Dibenzo[b,f]azocine
Kinase inhibitor

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2006.07.078

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abstract = "Synthetic routes towards highly substituted eight membered ring heterocycles fused to aryl rings such as the dibenzo[b,f]azocine system are still lacking. Herein, we present a convenient convergent synthetic route towards this heterocyclic class of compounds with possible variations at positions 4, 7, and 11. One member of a library of dibenzo[b,f]azocines with different substituents at position 11 was identified to inhibit protein kinase A activity (IC50 = 122 μM) but not protein kinase C.",

keywords = "Dibenzo[b,f]azocine, Kinase inhibitor",

author = "Arnold, {Leggy A.} and {Kiplin Guy}, R.",

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AU - Arnold, Leggy A.

AU - Kiplin Guy, R.

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N2 - Synthetic routes towards highly substituted eight membered ring heterocycles fused to aryl rings such as the dibenzo[b,f]azocine system are still lacking. Herein, we present a convenient convergent synthetic route towards this heterocyclic class of compounds with possible variations at positions 4, 7, and 11. One member of a library of dibenzo[b,f]azocines with different substituents at position 11 was identified to inhibit protein kinase A activity (IC50 = 122 μM) but not protein kinase C.

AB - Synthetic routes towards highly substituted eight membered ring heterocycles fused to aryl rings such as the dibenzo[b,f]azocine system are still lacking. Herein, we present a convenient convergent synthetic route towards this heterocyclic class of compounds with possible variations at positions 4, 7, and 11. One member of a library of dibenzo[b,f]azocines with different substituents at position 11 was identified to inhibit protein kinase A activity (IC50 = 122 μM) but not protein kinase C.

KW - Dibenzo[b,f]azocine

KW - Kinase inhibitor

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Synthesis of highly substituted dibenzo[b,f]azocines and their evaluation as protein kinase inhibitors

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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