120870-44-2

Upstream product

• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 90-02-8 salicylaldehyde 
• 122-59-8 2-phenoxyacetic acid 
• 97871-86-8 (Z)-2-(2-methoxybenzylidene)benzofuran-3(2H)-one 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 61370-67-0 2-(2-methoxybenzylidene)coumaran-3-one 

Relevant academic research and scientific papers

Polyphenolic glycosides and oligosaccharide multiesters from the roots of Polygala dalmaisiana

Four new polyphenolic glycosides, dalmaisiones A-D (1-4), 16 new oligosaccharide multiesters, dalmaisioses A-P (5, 7-21), and one known tetrasaccharide multiester, reiniose G (6), were isolated from the roots of Polygala dalmaisiana. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease

To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure-activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-α-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-α-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-κB transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-α gene, with compound 55 showing better efficacy. This inhibition of TNF-α expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-α expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose-dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD.

Suppression of LPS-induced NF-κB activity in macrophages by the synthetic aurone, (Z)-2-((5-(hydroxymethyl) furan-2-yl) methylene) benzofuran-3(2H)-one

Suppressing cytokine responses has frequently been shown to have promising therapeutic effects for many chronic inflammatory and autoimmune diseases. However, the severe side effects associated with the long-term use of current treatments, such as allergi

Antifungal activity of substituted aurones

Novel antifungals are in high demand as there is a growing resistance to antifungals currently in use. In particular, opportunistic fungal infections caused by Candida spp. are on the rise with infections by this genus accounting for the most severe funga

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.

Composition for preventing or treating inflammatory bowel disease comprising benzylidene benzofuranone compound as an active ingredient

The present invention relates to a composition for preventing and treating inflammatory bowel disease comprising a benzylidene benzofuranone derivative compound as an active ingredient. The benzylidene benzofuranone derivative compound is effective in maintaining the thickness of small intestine and the length of large intestine to normal states, and inhibiting inflammation with respect to large intestine, thereby being used as a pharmaceutical composition for preventing and treating inflammatory bowel disease.

Aurones: Small molecule visible range fluorescent probes suitable for biomacromolecules

Aurones, derivatives of 2-benylidenebenzofuran-3 (2H)-one, are natural products that serve as plant pigments. There have been reports that some of these substances fluoresce, but little information about their optical properties is in the literature. In this report, series of aurone derivatives were synthesized as possible fluorescent probes that can be excited by visible light. We found that an amine substituent shifted the lowest energy absorption band from the near-UV to the visible region of the electromagnetic spectrum. Four amine-substituted aurone derivatives were synthesized to explore the effect of this substituent on the absorption and emission properties of the aurone chromophore. The emission maxima and intensities of the molecules are strongly dependent on the nature of the substituent and the solvent polarity. Overall, the emission intensity increases and the maximum wavelength decreases in less polar solvents; thus, the aurones may be useful probes for hydrophobic sites on biological molecules. A limited investigation with model protein, nucleic acid and fixed cells supports this idea. It is known that the sulfur analog of aurone can undergo photoinduced E/Z isomerization. This possibility was investigated for one of the aminoaurones, which was observed to reversible photoisomerize. The two isomers have similar absorption spectra, but the emission properties are distinct. We conclude that appropriately substituted aurones are potentially useful as biological probes and photoswitches. Springer Science+Business Media, LLC 2011.

Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity.

Versatile and expeditious synthesis of aurones via AuI-catalyzed cyclization

(Chemical Equation Presented) Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3′,4′-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4′-chloroaurone) were achieved.

Condensation Product of Salicylaldehyde and 2-Bromo-2'-hydroxyacetophenone: Revision of Structure

Reaction between salicylaldehyde and 2-bromo-2'-hydroxyacetophenone (1) gives 2-(2-hydroxybenzylidene)coumaran-3-one (5) rather than 2-(2-hydroxybenzoyl)benzofuran (2) as reported in a patented literature.