4376-58-3

Basic information

• Product Name: 2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-
• CAS NO: 4376-58-3
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• Mol File: 4376-58-3.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-(4376-58-3)
• EPA Substance Registry System: 2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-(4376-58-3)

Safety Data

• Hazardous Substances Data: 4376-58-3(Hazardous Substances Data)

Upstream product

• 121-33-5 vanillin 
• 99-93-4 4-Hydroxyacetophenone 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 91471-08-8 3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde 

Downstream Products

• 1047973-87-4 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone 
• 1428324-90-6 1-(5-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 
• 1415219-61-2 C₂₄H₂₂N₂O₄ 
• 1415219-30-5 1-(5-(4-((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)-3-(4-((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-4,5-dihydropyrazol-1-yl)ethanone 

Relevant articles and documents

Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization

Screening a natural product library of 850 compounds yield isoliquiritigenin as an effective anti-inflammatory agent by inhibiting the production of pro-inflammatory NO induced by Pam3CSK4, while its activity accompanied by toxicity. Further studies obtained the optimized isoliquiritigenin derivative SMU-B14, which can inhibit Pam3CSK4 triggered toll-like receptor 2 (TLR2) signaling with low toxicity and high potency. Preliminary mechanism studies indicated that SMU-B14 worked through TLR2/MyD88, phosphorylation of IKKα/β, leading to the reduce degradation of NF-κB related IKBα and p65 complex, then inhibited the production of inflammatory cytokines, such as TNF-α, IL-6, IL-1β both in human and murine cell lines. Subsequent polarization experiments showed SMU-B14 significant reversed the polarization of M1 phenotype primary macrophage activated by Pam3CSK4 in vitro, and reduced the infiltration of neutrophil and polarization of M1-type macrophage, decreased serum alanine transaminase (ALT), as a result protected liver from being injured in vivo. In summary, we obtained an optimized lead compound SMU-B14 and found it functionally blocked TLR2/MyD88/NF-κB signaling pathway to down-regulate the production of inflammatory cytokines resulted significant liver protection property.

PYRIMIDINONE DERIVATIVES AND USES THEREOF TO NEUTRALIZE THE BIOLOGICAL ACTIVITY OF CHEMOKINES

A subject of the present invention is a compound having the general formula (I) a pharmaceutically acceptable salt thereof or a tautomeric form thereof, wherein A, B3, B4, B5, Y, X, B1 and B2 are as defined in any one of claims 1 to 10. Another subject of the invention is the compound as defined above for use as a medicament, in particular for preventing and/or treating inflammation and inflammatory diseases, immune and auto-immune diseases, pain related diseases, genetic diseases and/or cancer.

Facile Microwave-assisted Synthesis of 1,3,5-Trisubstituted Pyrazoline Derivatives Incorporating Sulfonyl Moiety

We developed an environmentally benign, convenient microwave-assisted process for the construction of 1,3,5-trisubstitued pyrazolines (10a～10f, 11a～11f, 12a～12f, 13a～13f). Chalcones, as the key intermedi- ates, were obtained by the condensation of each of appropriately substituted aromatic aldehydes (1～4) with 4-substituted acetophenones (5a～5f) via a Claisen-Schmidt reaction under the action of microwave irradiation. Cyclization of the chalcones (6a～6f, 7a～7f, 8a～8f, 9a～9f) with p-toluene sulfonhydrazide af- forded 1,3,5-trisubstitued pyrazoline derivatives using microwave-assisted process in 25 min and 140 watt power in glycol. The structures of targeted compounds were established by IR, 1H NMR, MS and ele- mental analysis. The results indicate that microwave-assisted synthetic process presents advantages in terms of enhancement in rate, decrease in reaction time, clean reaction and convenient operation.