Convenient synthetic method for 3-(3-substituted indol-2-yl)quinoxalin-2-ones as VEGF inhibitor.

doi:10.1248/CPB.55.922

Paper

Convenient synthetic method for 3-(3-substituted indol-2-yl)quinoxalin-2-ones as VEGF inhibitor.

Published Jun 1, 2007 · K. Aoki, Jyun-ichi Koseki, S. Takeda

Chemical & pharmaceutical bulletin

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Abstract

It has already been reported that 3-(indol-2-yl)quinoxalin-2-ones have a potent inhibitory effect on the growth of tumor cells based on anti-angiogenesis activity. We have also carried out a structure-activity relationship (SAR) study of 3-(indol-2-yl)quinoxalin-2-ones, which showed a potent inhibitory activity toward the vascular endothelial growth factor (VEGF)-induced proliferation of human mesangial cells and the VEGF-induced auto-phosphorylation of human umbilical vein endothelial cells. Moreover, one of these compounds has a potent medicinal effect based on anti-angiogenic action, by oral administration (Chart 1, 9). However, since the existing synthetic methods for the preparation of 3-(indol-2-yl)quinoxalin-2-ones consist of multiple steps some of which require strict anhydrous conditions, a convenient and simple synthetic method in place of the existing method is desirable. As a result of the investigations into the synthetic procedures, 3-(3-substituted indol-2-yl)quinoxalin-2-ones can be easily prepared by the condensation of 3-substituted indoles with quinoxalin-2-ones in the presence of trifluoroacetic acid (TFA). Herein, we report the examination of these reaction conditions and the application of this new synthetic method to the synthesis of the derivatives as VEGF inhibitors.

Study Snapshot

This study presents a new, convenient synthetic method for 3-(3-substituted indol-2-yl)quinoxalin-2-ones, which show potential as VEGF inhibitors, by condensation of 3-substituted indoles with quinoxalin-2-ones

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Convenient synthetic method for 3-(3-substituted indol-2-yl)quinoxalin-2-ones as VEGF inhibitor.

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References

Potent platelet-derived growth factor-beta receptor (PDGF-betaR) inhibitors: Synthesis and structure-activity relationships of 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl}quinoxalin-2(1H)-one derivatives.

7d-9, a novel PDGF-betaR inhibitor, shows potent and selective activity against various growth factors, offering potential therapeutic applications.

Highly Diastereoselective Synthesis of 3-Indolyl-N-Substituted Glycine Derivatives via TFA-Promoted Friedel—Crafts Type Reaction of Indoles with Chiral Cyclic Glyoxylate Imine.

This study presents a highly diastereoselective method for the synthesis of 3-indolyl-N-substituted glycine derivatives using indoles and chiral cyclic glyoxylate imines in the presence of TFA.

THE PREPARATION OF THE HYDROXYSKATOLES AND 5,6-DIHYDROXYSKATOLE

This study presents a new method for preparing hydroxyskatoles and 5,6-dihydroxyskatole, using 4-, 5-, 6-, and 7-benzyloxyindole-3-carboxaldehyde and 5,6-dibenzyloxyindole-3-car

Synthesis of aromatic aldehydes via 2-aryl-n,n'-diacyl-4-imidazolines

This study presents a new method for synthesizing aromatic aldehydes using 2-aryl-n,n'-diacyl-4-imidazolines, with a synthetic scope similar to the Vilsmeier-Haack reaction.

Citations

Mild Iron-Catalyzed Oxidative Cross-Coupling of Quinoxalinones with Indoles

This study developed a mild oxidative cross-coupling reaction between quinoxalinones and indoles, yielding versatile 3-(indol-3-yl)quinoxalin-2-one derivatives with high yields and cost-effectiveness.

Divergent Synthesis of 3-(Indol-2-yl)quinoxalin-2-ones and 4-(Benzimidazol-2-yl)-3-methyl(aryl)cinnolines via Polyphosphoric Acid (PPA)-Mediated Intramolecular Rearrangements of 3-(Methyl/aryl(2-phenylhydrazono)methyl)quinoxalin-2-ones.

Polyphosphoric acid-mediated divergent metal-free synthesis allows for rapid access to diverse 3-(indol-2-yl)quinoxalin-2-ones and 4-(benzimidazol-2-yl)-3-methylcinnolines, offering potential for unique compound libraries in drug design and

Direct C3-H carbamoylation of quinoxalin-2(1H)-ones with isocyanides enabled by selectfluor II under mild conditions

Selectfluor II-mediated direct C-H carbamoylation of quinoxalin-2(1H)-ones under mild conditions allows for the synthesis of 42 new compounds and is environmentally friendly.

Recent Advances in Photocatalytic Functionalization of Quinoxalin‐2‐ones

Visible-light photofunctionalization of quinoxalin-2-one derivatives has advanced, enabling the synthesis of biologically active compounds with various bond types.

tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions.

This study presents an efficient and atom-economical method for C-3 functionalization of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone, and 2-hydroxy-1,4-naphthoquinone under metal-free conditions, yield