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Molecules 2018, 23(1), 221; https://doi.org/10.3390/molecules23010221

A Diverse and Versatile Regiospecific Synthesis of Tetrasubstituted Alkylsulfanylimidazoles as p38α Mitogen-Activated Protein Kinase Inhibitors

1
Institute of Pharmaceutical Sciences, Department of Medicinal and Pharmaceutical Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany
2
Teva-ratiopharm, Graf-Arco-Str. 3, 89079 Ulm, Germany
*
Author to whom correspondence should be addressed.
Received: 12 December 2017 / Revised: 16 January 2018 / Accepted: 17 January 2018 / Published: 20 January 2018
(This article belongs to the Section Organic Chemistry)
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Abstract

An alternative strategy for the synthesis of 1-aryl- and 1-alkyl-2-methylsulfanyl-4-(4-fluorophenyl)-5-(pyridin-4-yl)imidazoles as potential p38α mitogen-activated protein kinase inhibitors is reported. The regioselective N-substitution of the imidazole ring was achieved by treatment of α-aminoketones with different aryl or alkyl isothiocyanates. In contrast to previously published synthesis routes starting from 2-amino-4-methylpyridine, the presented route is characterized by a higher flexibility and a lower number of steps. This strategy was also applied to access 1-alkyl-2-methylsulfanyl-5-(4-fluorophenyl)-4-(pyridin-4-yl)imidazoles in six steps starting from 2-chloro-4-methylpyridine. View Full-Text
Keywords: regiospecific synthesis; tetrasubstituted imidazoles; p38α MAP kinase regiospecific synthesis; tetrasubstituted imidazoles; p38α MAP kinase
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Ansideri, F.; Andreev, S.; Kuhn, A.; Albrecht, W.; Laufer, S.A.; Koch, P. A Diverse and Versatile Regiospecific Synthesis of Tetrasubstituted Alkylsulfanylimidazoles as p38α Mitogen-Activated Protein Kinase Inhibitors. Molecules 2018, 23, 221.

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