2,6-Di(arylamino)-3-fluoropyridine derivatives as HIV non-nucleoside reverse transcriptase inhibitors

Sergey Sergeyev, Ashok Kumar Yadav, Philippe Franck, Johan Michiels, Paul Lewi, Jan Heeres, Guido Vanham, Kevin K Ariën, Christophe M L Vande Velde, Hans De Winter, Bert U W Maes

Research output: Contribution to journalA1: Web of Science-article

Abstract

New non-nucleoside reverse transcriptase inhibitors (NNRTI), which are similar in structure to earlier described di(arylamino)pyrimidines but featuring a 2,6-di(arylamino)-3-fluoropyridine, 2,4-di(arylamino)-5-fluoropyrimidine, or 1,3-di(arylamino)-4-fluorobenzene moiety instead of a 2,4-disubstituted pyrimidine moiety, are reported. The short and practical synthesis of novel NNRTI relies on two sequential Pd-catalyzed aminations as the key steps. It is demonstrated through direct comparison with reference compounds that the presence of a fluorine atom increases the in vitro anti-HIV activity, both against the wild type virus and drug-resistant mutant strains.

Original languageEnglish
JournalJournal of Medicinal Chemistry
Volume59
Issue number5
Pages (from-to)1854-1868
ISSN0022-2623
DOIs
Publication statusPublished - 2016

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