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Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
Author(s) -
Ouahrouch Abdelaaziz,
Taourirte Moha,
Schols Dominique,
Snoeck Robert,
Andrei Graciela,
Engels Joachim W.,
Lazrek Hassan B.
Publication year - 2016
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201500292
Subject(s) - cycloaddition , chemistry , alkyne , catalysis , stereochemistry , azide , biological activity , virus , combinatorial chemistry , organic chemistry , biochemistry , in vitro , virology , biology
A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I 2 as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by 1 H NMR, 13 C NMR, and HRMS spectra. The structures of 2e , 2f , 3d , and 3g were further confirmed by X‐ray diffraction analysis. These compounds were tested against various strains of DNA and RNA viruses; compounds 4b and 4c showed a modest inhibitory activity against respiratory syncytial virus (RSV) and compound 4h displayed modest inhibitory activity against Coxsackie virus B4.