Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

A two-step palladium-catalyzed procedure based on Suzuki–Miyaura cross coupling, followed by a double Buchwald–Hartwig reaction, allows for the synthesis of pharmaceutically relevant benzo[4,5]furo[3,2-b]indoles in moderate to very good yield. The synthesized compounds have been analyzed with regard...

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Autores principales: Do, Hoang Huy, Ullah, Saif, Villinger, Alexander, Lecka, Joanna, Sévigny, Jean, Ehlers, Peter, Iqbal, Jamshed, Langer, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6880817/
https://www.ncbi.nlm.nih.gov/pubmed/31807218
http://dx.doi.org/10.3762/bjoc.15.276
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author Do, Hoang Huy
Ullah, Saif
Villinger, Alexander
Lecka, Joanna
Sévigny, Jean
Ehlers, Peter
Iqbal, Jamshed
Langer, Peter
author_facet Do, Hoang Huy
Ullah, Saif
Villinger, Alexander
Lecka, Joanna
Sévigny, Jean
Ehlers, Peter
Iqbal, Jamshed
Langer, Peter
author_sort Do, Hoang Huy
collection PubMed
description A two-step palladium-catalyzed procedure based on Suzuki–Miyaura cross coupling, followed by a double Buchwald–Hartwig reaction, allows for the synthesis of pharmaceutically relevant benzo[4,5]furo[3,2-b]indoles in moderate to very good yield. The synthesized compounds have been analyzed with regard to their inhibitory activity (IC(50)) of nucleotide pyrophosphatases h-NPP1 and h-NPP3. The activity lies in the nanomolar range. The results were rationalized based on docking studies.
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spelling pubmed-68808172019-12-05 Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles Do, Hoang Huy Ullah, Saif Villinger, Alexander Lecka, Joanna Sévigny, Jean Ehlers, Peter Iqbal, Jamshed Langer, Peter Beilstein J Org Chem Full Research Paper A two-step palladium-catalyzed procedure based on Suzuki–Miyaura cross coupling, followed by a double Buchwald–Hartwig reaction, allows for the synthesis of pharmaceutically relevant benzo[4,5]furo[3,2-b]indoles in moderate to very good yield. The synthesized compounds have been analyzed with regard to their inhibitory activity (IC(50)) of nucleotide pyrophosphatases h-NPP1 and h-NPP3. The activity lies in the nanomolar range. The results were rationalized based on docking studies. Beilstein-Institut 2019-11-22 /pmc/articles/PMC6880817/ /pubmed/31807218 http://dx.doi.org/10.3762/bjoc.15.276 Text en Copyright © 2019, Do et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Do, Hoang Huy
Ullah, Saif
Villinger, Alexander
Lecka, Joanna
Sévigny, Jean
Ehlers, Peter
Iqbal, Jamshed
Langer, Peter
Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
title Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
title_full Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
title_fullStr Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
title_full_unstemmed Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
title_short Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
title_sort palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6880817/
https://www.ncbi.nlm.nih.gov/pubmed/31807218
http://dx.doi.org/10.3762/bjoc.15.276
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