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Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259
Graphical Abstract
Figure 1: Natural products having a 1,2,4-oxadiazole core.
Figure 2: Examples of 1,2,4-oxadiazole antitumorals.
Scheme 1: Common synthetic strategies toward 1,2,4-oxadiazoles; (a) amidoxime route; (b) 1,3 dipolar cycloadd...
Scheme 2: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the amidoxime route....
Figure 3: Molecular structure of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1). Atoms are drawn as 50% the...
Figure 4: Packing diagram of compound 1. Hydrogen bonds are indicated as dashed lines.
Scheme 3: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the 1,3-dipolar cycl...
Figure 5: Molecular structure of 3-tert-butyl-5-(4-nitrophenyl)-1,2,4-oxadiazole (2). Atoms are drawn as 50% ...
Figure 6: Packing diagram of compound (2) showing C–H···O interactions.
Scheme 4: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4).
Figure 7: Molecular structure of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4). At...
Figure 8: Molecular structure of 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4 oxobutanoate (5). Ato...
Figure 9: Packing diagram of compound (5). Dashed lines indicate hydrogen bonds.
Scheme 5: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7).
Figure 10: Molecular structure of (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic ac...
Figure 11: Packing diagram of compound 6. Dashed lines indicate hydrogen bonds.
Figure 12: In vitro antitumor activity of compounds 1, 3–7 toward 11 human tumor cell lines.
Figure 13: Individual IC50 values [µM] of compounds 1, 3–7 in a panel of 11 human tumor cell lines.