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

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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Main Authors: Hoang Huy Do, Saif Ullah, Alexander Villinger, Joanna Lecka, Jean Sévigny, Peter Ehlers, Jamshed Iqbal, Peter Langer
Format: Article
Language:English
Published: Beilstein-Institut 2019-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
buchwald–hartwig reaction
cyclization
n-heterocycles
palladium
suzuki–miyaura reaction
Online Access:https://doi.org/10.3762/bjoc.15.276
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spelling doaj-f1bf352647514929b0f1336177ca268f2021-02-02T07:13:42ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-11-011512830283910.3762/bjoc.15.2761860-5397-15-276Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indolesHoang Huy Do0Saif Ullah1Alexander Villinger2Joanna Lecka3Jean Sévigny4Peter Ehlers5Jamshed Iqbal6Peter Langer7Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, GermanyCentre for Advanced Drug Research, COMSATS University Islamabad, Abbottabad Campus, Abbottabad-22060, PakistanInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, GermanyDépartement de microbiologie-infectiologie et d'immunologie, Faculté de Médecine, Université Laval, Québec, QC, G1V 0A6, CanadaDépartement de microbiologie-infectiologie et d'immunologie, Faculté de Médecine, Université Laval, Québec, QC, G1V 0A6, CanadaInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, GermanyCentre for Advanced Drug Research, COMSATS University Islamabad, Abbottabad Campus, Abbottabad-22060, PakistanInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, GermanyA 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 (IC50) of nucleotide pyrophosphatases h-NPP1 and h-NPP3. The activity lies in the nanomolar range. The results were rationalized based on docking studies.https://doi.org/10.3762/bjoc.15.276buchwald–hartwig reactioncyclizationn-heterocyclespalladiumsuzuki–miyaura reaction
collection DOAJ
language English
format Article
sources DOAJ
author Hoang Huy Do
Saif Ullah
Alexander Villinger
Joanna Lecka
Jean Sévigny
Peter Ehlers
Jamshed Iqbal
Peter Langer
spellingShingle Hoang Huy Do
Saif Ullah
Alexander Villinger
Joanna Lecka
Jean Sévigny
Peter Ehlers
Jamshed Iqbal
Peter Langer
Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
Beilstein Journal of Organic Chemistry
buchwald–hartwig reaction
cyclization
n-heterocycles
palladium
suzuki–miyaura reaction
author_facet Hoang Huy Do
Saif Ullah
Alexander Villinger
Joanna Lecka
Jean Sévigny
Peter Ehlers
Jamshed Iqbal
Peter Langer
author_sort Hoang Huy Do
title 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_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_sort palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2019-11-01
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 (IC50) of nucleotide pyrophosphatases h-NPP1 and h-NPP3. The activity lies in the nanomolar range. The results were rationalized based on docking studies.
topic buchwald–hartwig reaction
cyclization
n-heterocycles
palladium
suzuki–miyaura reaction
url https://doi.org/10.3762/bjoc.15.276
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