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Synthesis 2017; 49(16): 3692-3699
DOI: 10.1055/s-0036-1588780
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 5-Arylpyrrole-2-carboxylic Acids as Key Intermediates for NBD Series HIV-1 Entry Inhibitors

Dmitry S. Belov
a   EDASA Scientific, Scientific Park, Moscow State University, Leninskie Gory, Bld. 75, 77−101b, 119992 Moscow, Russian Federation
,
Vladimir N. Ivanov
a   EDASA Scientific, Scientific Park, Moscow State University, Leninskie Gory, Bld. 75, 77−101b, 119992 Moscow, Russian Federation
,
Francesca Curreli
b   Laboratory of Molecular Modeling and Drug Design, Lindsey F. Kimball Research Institute, New York Blood Center, New York, New York 10065, USA   Email: adebnath@nybc.org
,
Alexander V. Kurkin
a   EDASA Scientific, Scientific Park, Moscow State University, Leninskie Gory, Bld. 75, 77−101b, 119992 Moscow, Russian Federation
,
Andrea Altieri
a   EDASA Scientific, Scientific Park, Moscow State University, Leninskie Gory, Bld. 75, 77−101b, 119992 Moscow, Russian Federation
,
Asim K. Debnath  *
b   Laboratory of Molecular Modeling and Drug Design, Lindsey F. Kimball Research Institute, New York Blood Center, New York, New York 10065, USA   Email: adebnath@nybc.org
› Author AffiliationsSupported by: National Institutes of Health, USA (RO1 AI104416)
Further Information

Publication History

Received: 22 February 2017

Accepted after revision: 19 March 2017

Publication Date:
18 April 2017 (online)

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Abstract

5-Arylpyrrole-2-carboxylic acids are important key intermediates in the synthesis of HIV-1 entry inhibitors (such as NBD-11021 and NBD-14010). Here we present a general method for the synthesis of some 5-arylpyrrole-2-carboxylic acids in three steps starting from pyrrole. By this method, the compounds could be prepared on gram scale and without chromatographic purification.

Key words

HIV-1 entry inhibitors - pyrroles - carboxylic acids - arylation - trifluoroacetylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588780.
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