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1 article(s) from Sun, Qiu

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

Qiu Sun,
Jörg Heilmann and
Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

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Graphical Abstract

Figure 1: Structure of 4-hydroxybenzyl alcohol (HBA, 1).

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Figure 2: Structure–activity relationship of curcumin analogs.

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Scheme 1: Synthesis of curcumin (3). Reagents and conditions: (a) vanillin, 1,2,3,4-tetrahydroquinoline, HOAc...

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Figure 3: Backbone and substitution of monocarbonyl analogs of curcumin (MACs) showing their structural diver...

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Scheme 2: Exemplary synthesis of MAC representatives. Reagents and conditions: (a) 40% KOH, EtOH, 5 °C; stirr...

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Scheme 3: Synthesis of ellagic acid (7). Reagents and conditions: (a) H₂SO₄, CH₃OH; (b) (1) o-chloranil, Et₂O...

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Figure 4: Structure of resveratrol and its analogs.

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Scheme 4: Synthesis of quinolone-substituted phenol 20. Reagents and conditions: (a) Ac₂O, 2-hydroxybenzaldeh...

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Scheme 5: Synthesis of quinolone-substituted phenol 23. Reagents and conditions: (a) Ac₂O, 2-hydroxybenzaldeh...

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Figure 5: Design of 4-amino-2-sulfanylphenol derivatives and their structure–activity relationship.

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Scheme 6: Synthesis of 4-amino-2-sulfanylphenol derivatives. Reagents and conditions: (a) R¹SO₂Cl, pyridine, ...

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Figure 6: Structures of two series of natural-like acylphloroglucinols.

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Scheme 7: Synthesis of acylphloroglucinol derivatives 35–41. Reagents and conditions: (a) acyl chloride, AlCl₃...

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Scheme 8: Synthesis of acylphloroglucinol derivatives 43–51. Reagents and conditions: (a) isoprene, Amberlyst...

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Figure 7: Analogs of (−)-EGCG for the prevention of oxidation and improvement of the bioavailability of the c...

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Scheme 9: Synthesis of xanthohumol 58. Reagents and conditions: (a) MOMCl, diisopropylethylamine, CH₂Cl₂; (b)...

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Scheme 10: Synthesis of genistein 60. Reagents and conditions: (a) 4-hydroxyphenylacetonitrile, anhydrous HCl,...

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Scheme 11: Synthesis of fisetin (67) and quercetin (68). Reagents and conditions: (a) 3,4-dimethoxybenzaldehyd...

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Figure 8: Structure of (2S)-7,2’,4’-trihydroxy-5-methoxy-8-(dimethylallyl)flavanone (69).

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Review

Published 16 Feb 2015

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