TY - JOUR
T1 - 2,6-Di(arylamino)-3-fluoropyridine derivatives as HIV non-nucleoside reverse transcriptase inhibitors
AU - Sergeyev, Sergey
AU - Yadav, Ashok Kumar
AU - Franck, Philippe
AU - Michiels, Johan
AU - Lewi, Paul
AU - Heeres, Jan
AU - Vanham, Guido
AU - Ariën, Kevin K
AU - Vande Velde, Christophe M L
AU - De Winter, Hans
AU - Maes, Bert U W
N1 - PPU
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
U2 - 10.1021/acs.jmedchem.5b01336
DO - 10.1021/acs.jmedchem.5b01336
M3 - A1: Web of Science-article
C2 - 26785139
SN - 0022-2623
VL - 59
SP - 1854
EP - 1868
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 5
ER -