59817-22-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one is used as a pharmaceutical agent for its potential antioxidant, anti-inflammatory, and anticancer properties. 1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one's pharmacological activities make it a candidate for the development of new drugs targeting various diseases, including cancer and neurodegenerative conditions.
Used in Research and Development:
In the field of medicinal chemistry, 1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one is used as a subject of study for its potential applications in drug discovery and development. 1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one's unique structure and pharmacological properties are of interest to researchers seeking to understand its full potential and develop new therapeutic strategies.
Used in Nutraceutical Industry:
Given its antioxidant properties, 1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one may also be used as an ingredient in the nutraceutical industry for the development of dietary supplements and functional foods aimed at promoting health and wellness.

InChI:InChI=1/C18H18O5/c1-21-16-10-12(11-17(22-2)18(16)23-3)8-9-15(20)13-6-4-5-7-14(13)19/h4-11,19H,1-3H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 875467-91-7 (+/-)-3-hydroxymethyl-3-(3',4',5'-trimethoxybenzyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 154542-32-2 3-Hydroxy-3',4',5'-trimethoxyflavone 
• 1141392-65-5 C₁₈H₂₀N₂O₄ 
• 127956-54-1 3-(3,4,5-Trimethoxy-benzyl)-chromen-4-one 
• 927429-55-8 Z-2-[(2,4,5-trimethoxyphenyl)methylene]benzo[b]furan-3-one 
• 71906-92-8 2,3-dihydro-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one 
• 127956-53-0 1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)-1-propanone 
• 67858-30-4 2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Substitution effect on a hydroxylated chalcone: Conformational, topological and theoretical studies

The effect of substituents on two hydroxylated chalcones was studied in this work. The first chalcone, with a dimethylamine group (HY-DAC) and the second, with three methoxy groups (HY-TRI) were synthesized and crystallized from ethanol on centrosymmetric

Antischistosomal properties of aurone derivatives against juvenile and adult worms of Schistosoma mansoni

Schistosomiasis is a neglected disease caused by helminth flatworms of the genus Schistosoma, affecting over 240 million people in more than 70 countries. The treatment relies on a single drug, praziquantel, making urgent the discovery of new compounds. A

Design, synthesis, and biological evaluation of Helicobacter pylori inosine 5′-monophosphate dehydrogenase (HpIMPDH) inhibitors

Inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of 23 new chemical entities (NCEs) with substituted flavone (Series 1) and 1,2,3-triazole (Series 2) core structures for their in vitro Helicobacter pylori IMPDH (HpIMPDH) and human IMPDH2 (hIMPDH2) inhibitory activities. All the NCEs possessed acceptable molecular, physicochemical, and toxicity property profiles. The ranges for HpIMPDH and hIMPDH2 inhibition were 9–99.9% and 16–57%, respectively, at 10 μM concentration. The most potent HpIMPDH inhibitor, 25c, exhibited IC50 value of 1.27 μM with no hIMPDH2 inhibitory activity. The moderately potent, structurally novel hit molecule, 25c, may serve as a lead for further design and development of highly potent HpIMPDH inhibitors.

Design and characterization of highly in vitro antitumor active ternary copper(II) complexes containing 2′-hydroxychalcone ligands

A series of innovative copper(II) complexes of the general composition [Cu(Ln)(phen)]NO3 (1–8; phen?=?1,10-phenanthroline), involving 2′-hydroxychalcone {(E)-1-(2′-hydroxyphenyl)-3-phenylprop-2-en-1-one} derivatives (HLn)

Synthesis and anti-cancer activity evaluation of new dimethoxylated chalcone and flavanone analogs

A novel series of chalcones and flavanones discriminated by the presence of a 3,4-dimethoxyphenyl moiety in their structures were synthesized as anti-cancer agents. The cytotoxicity evaluation of the analogs against the MCF-7, MDA-MB-231 (human breast can

Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic proteins

In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-lymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, Bcl-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, sTNF-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated.

Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin

A series of chalcone and flavonol derivatives were synthesized in good yield by an eco-friendly approach. A pharmacological evaluation was performed with the human colorectal carcinoma cell line HCT116 and revealed that the anticancer activity of flavonols was higher when compared with that of the respective chalcone precursors. The antiproliferative activity of halogenated derivatives increases as the substituent in the 3- or 4-positon of the B-ring goes from F to Cl and to Br. In addition, halogens in position 3 enhance anticancer activity in chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully prepared and presented high anticancer activity as shown by their cell growth and cell cycle inhibitory potential against HCT116 cells, superior to that of quercetin, used as a positive control.

Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics

A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4′-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2′,2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA.

Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study

A series of 2′-hydroxychalcones has been synthesized and screened for their in vitro inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells. Structure-activity relationship study suggested that inhibitory activity against prostaglandin E2 production was governed to a greater extent by the substituent on B ring of the chalcone, and most of the active compounds have at least two methoxy or benzyloxy groups on B ring. The relationship between chalcone structures and their PGE2 inhibitory activities was also interpreted by docking study on cyclooxygenase-2.

Synthesis of a library of glycosylated flavonols

Flavonols are an important class of natural products isolated from plants. Some glycosylated flavonols showed very interesting biological activities. A library of flavonols has been made through Algar-Flynn-Oyamada reaction from 2′-hydroxyacetophenones an