112980-33-3

Upstream product

• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 65786-13-2 2'-hydroxy-4-dimethylaminochalcone 
• 65786-13-2 (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 118-93-4 o-hydroxyacetophenone 

Relevant academic research and scientific papers

Synthesis, crystal structure and two-photon excited fluorescence properties of three aurone derivatives

Three aurone derivatives, Z-2-[(4-N,N-dimethylaminophenyl)methylene] benzofuran-3-one (1), Z-2-[(N-ethylcarbazol-3-yl)methylene]benzofuran-3-one (2) and Z-2-[(pyren-1-yl)methylene]benzofuran-3-one (3) have been synthesized by the cyclization of 2′-hydroxy

Aurone Derivative Revealing the Metabolism of Lipid Droplets and Monitoring Oxidative Stress in Living Cells

Lipid droplets (LDs) are closely connected to many physiological processes and abnormal LDs are related to many diseases. Herein, a family of two-photon fluorescence compounds based on the aurone skeleton were developed as efficient LDs imaging probes. They exhibit the obvious solvatochromism effect from blue to orange emission (～140 nm shift) in various solvents. The robust probes possess low toxicity to living cells, high photobleaching resistance, and superior photostability and can light up LDs with high specificity. Furthermore, the probe DMMB (aurone skeleton with dimethylamino) was carefully applied in real-time monitoring of the morphological changes of LDs and the interactions between LDs and mitochondria under specific physiological conditions (e.g., starvation). We have observed for the first time the dynamic change between mitochondria and LDs when mitochondrial damage is caused by a large excess of H2O2 in a short period of time.

"On water" synthesis of aurones: First synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia

A simple and green method for the synthesis of aurones by condensation of benzofuranone with aromatic aldehyde in neat water has been developed. The main advantages of this protocol include good yields, absence of catalyst, reagent, organic solvent, work-up and chromatographic purification. 4,5,3',4',5'-Pentamethoxy-6-hydroxyaurone, isolated from Smilax riparia was synthesized for the first time from 3-benzyloxy-4,5-dimethoxybenzaldehyde in five steps. {figure presented}.

THERAPEUTIC AURONES

Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

Probing the aurone scaffold against Plasmodium falciparum: Design, synthesis and antimalarial activity

A library comprising 44 diversely substituted aurones derivatives was synthesized by straightforward aldol condensation reactions of benzofuranones and the appropriately substituted benzaldehydes. Microwave enhanced synthesis using palladium catalyzed protocols was introduced as a powerful strategy for extending the chemical space around the aurone scaffold. Additionally, Mannich-base derivatives, containing a 7-aminomethyl-6-hydroxy substitution pattern at ring A, were also prepared. Screening against the chloroquine resistant Plasmodium falciparum W2 strain identified novel aurones with IC 50 values in the low micromolar range. The most potent compounds contained a basic moiety, with the ability to accumulate in acidic digestive vacuole of the malaria parasite. However, none of those aurones revealed significant activity against hemozoin formation and falcipain-2, two validated targets expressed during the blood stage of P. falciparum infection and functional in digestive vacuole of the parasite. Overall, this study highlight (i) the usefulness of aurones as platforms for synthetic procedures using palladium catalyzed protocols to rapidly deliver lead compounds for further optimization and (ii) the potential of novel aurone derivatives as promising antimalarial compounds.

Synthesis, structural revision, and biological activities of 4′-chloroaurone, a metabolite of marine brown alga Spatoglossum variabile

4′-Chloroaurone (1a), the only aurone reported from a marine source, Spatoglossum variabile was synthesized from 2-hydroxyacetophenone along with six structural analogs. The products obtained were Z-isomers and these were converted into E-isomers by photo

ALUMINA-MEDIATED CONDENSATION. A SIMPLE SYNTHESIS OF AURONES

A simple and high yielding synthesis of aurones (2-phenylmethylene-3(2H)-benzofuranones) is described which occurs under mild conditions on alumina surface using readily available benzofuranones and arylaldehydes.Key Words: Aurones; 2-Phenylmethylene-3(2H)-benzofuranones; Solid Surface; Alumina

FLAVONOIDS, XXXVII. RING CONTRACTION AND RING ENLARGEMENT REACTIONS WITH TRIMETHYLSILYL AZIDE IN THE FIELD OF FLAVONOIDS

The reaction of flavanone with trimethylsilyl azide (TMSA) in trifluoroacetic acid (TFA) afforded by ring expansion, 2,3-dihydro-2-phenyl-1,4-benzoxazepin-5(4H)-one or 2,3-dihydro-2-phenyl-4H-tetrazolo-1,4-benzoxazepine.The same products could be isolated using sodium azide in TFA.An unknown intermediate of the Schmidt reaction was also isolated.Treatment of 2'-hydroxychalcone with TMSA or sodium azide in TFA resulted in isoflavone and trans-3-aminoflavanone.The reaction of 4-substituted 2'-hydroxychalcones with TMSA in dimethylformamide gave, with ring contraction, aurones and flavones.