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

ABSTRACT: 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.

SUBMITTER: Do HH 

PROVIDER: S-EPMC6880817 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Do Hoang Huy HH   Ullah Saif S   Villinger Alexander A   Lecka Joanna J   Sévigny Jean J   Ehlers Peter P   Iqbal Jamshed J   Langer Peter P  

Beilstein journal of organic chemistry 20191122

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<i>-b</i>]indoles in moderate to very good yield. The synthesized compounds have been analyzed with regard to their inhibitory activity (IC<sub>50</sub>) of nucleotide pyrophosphatases <i>h</i>-NPP1 and <i>h</i>-NPP3. The activity lies in the nanomolar range. The results were rationalized based on  ...[more]

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