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1 article(s) from Fiebig, Heiner

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

Catalin V. Maftei,
Elena Fodor,
Peter G. Jones,
M. Heiko Franz,
Gerhard Kelter,
Heiner Fiebig and
Ion Neda

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

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Graphical Abstract

Figure 1: Natural products having a 1,2,4-oxadiazole core.

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Figure 2: Examples of 1,2,4-oxadiazole antitumorals.

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Scheme 1: Common synthetic strategies toward 1,2,4-oxadiazoles; (a) amidoxime route; (b) 1,3 dipolar cycloadd...

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Scheme 2: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the amidoxime route....

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Figure 3: Molecular structure of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1). Atoms are drawn as 50% the...

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Figure 4: Packing diagram of compound 1. Hydrogen bonds are indicated as dashed lines.

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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...

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Figure 5: Molecular structure of 3-tert-butyl-5-(4-nitrophenyl)-1,2,4-oxadiazole (2). Atoms are drawn as 50% ...

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Figure 6: Packing diagram of compound (2) showing C–H···O interactions.

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Scheme 4: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4).

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Figure 7: Molecular structure of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4). At...

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Figure 8: Molecular structure of 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4 oxobutanoate (5). Ato...

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Figure 9: Packing diagram of compound (5). Dashed lines indicate hydrogen bonds.

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Scheme 5: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7).

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Figure 10: Molecular structure of (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic ac...

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Figure 11: Packing diagram of compound 6. Dashed lines indicate hydrogen bonds.

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Figure 12: In vitro antitumor activity of compounds 1, 3–7 toward 11 human tumor cell lines.

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Figure 13: Individual IC₅₀ values [µM] of compounds 1, 3–7 in a panel of 11 human tumor cell lines.

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Full Research Paper

Published 25 Oct 2013

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