2,6-Di(arylamino)-3-fluoropyridine Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors

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-disubs...

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Veröffentlicht in:Journal of medicinal chemistry 2016-03, Vol.59 (5), p.1854-1868
Hauptverfasser: Sergeyev, Sergey, Yadav, Ashok Kumar, Franck, Philippe, Michiels, Johan, Lewi, Paul, Heeres, Jan, Vanham, Guido, Ariën, Kevin K, Vande Velde, Christophe M. L, De Winter, Hans, Maes, Bert U. W
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/acs.jmedchem.5b01336