14227-15-7

Basic information

• Product Name: (2E)-1-(2',4',5'-trimethoxyphenyl)-3-phenyl-2-propen-1-one
• Synonyms: (2E)-1-(2',4',5'-trimethoxyphenyl)-3-phenyl-2-propen-1-one
• CAS NO: 14227-15-7
• Molecular Weight: 298.339
• Mol File: 14227-15-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2E)-1-(2',4',5'-trimethoxyphenyl)-3-phenyl-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(2',4',5'-trimethoxyphenyl)-3-phenyl-2-propen-1-one(14227-15-7)
• EPA Substance Registry System: (2E)-1-(2',4',5'-trimethoxyphenyl)-3-phenyl-2-propen-1-one(14227-15-7)

Safety Data

• Hazardous Substances Data: 14227-15-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 1818-28-6 2',4',5'-trimethoxyacetophenone 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 77-78-1 dimethyl sulfate 
• 40357-53-7 (E)-1-(2-hydroxy-4,5-dimethoxyphenyl)-3-phenylprop-2-en-1-one 
• 875213-77-7 1-(2,4,5-triacetoxy-phenyl)-ethanone 
• 7446-70-0 aluminium trichloride 
• 102-92-1 cinnamoyl chloride 
• 533-73-3 1,2,4-Trihydroxybenzene 

Relevant articles and documents

Methoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities

Background: Chalcones substituted by methoxyl groups have presented a broad spec-trum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by chalcones substituted by methoxyl groups on rings A (5–12) and B (13–21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antipro-liferative agents. 3’, 4’, 5’-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 μg/mL), eight times more potent than fluconazole (reference antifungal drug). 3’-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 μg/mL). 2’,5’-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 μM. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 μM. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacte-rial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and phar-macokinetics properties to the library of methoxychalcones.