103826-26-2

Basic information

• Product Name: 3-methyl,4'-hydroxychalcone
• Synonyms: 3-methyl,4'-hydroxychalcone
• CAS NO: 103826-26-2
• Molecular Weight: 238.286
• Mol File: 103826-26-2.mol

Chemical Properties

• CAS DataBase Reference: 3-methyl,4'-hydroxychalcone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl,4'-hydroxychalcone(103826-26-2)
• EPA Substance Registry System: 3-methyl,4'-hydroxychalcone(103826-26-2)

Safety Data

• Hazardous Substances Data: 103826-26-2(Hazardous Substances Data)

Upstream product

• 103826-21-7 (E)-3-m-Tolyl-acrylic acid phenyl ester 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 99-93-4 4-Hydroxyacetophenone 
• 620-23-5 m-tolyl aldehyde 

Relevant articles and documents

Synthesis and antibacterial evaluation of novel chalcone derivatives containing a benzothiazole scaffold

Abstract: A series of novel chalcone derivatives containing a benzothiazole scaffold were synthesized to develop novel antibacterial agents for solving the problem of drug resistance. Most compounds exhibited excellent antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), and Ralstonia solanacearum (Rs) compared to a reference drug, bismerthiazol. The results indicated that chalcone derivatives containing a benzothiazole scaffold merit more research as promising antibacterial agents. Graphical abstract: [Figure not available: see fulltext.].

Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues

Strobilurin derivatives have become one of the most important classes of agricultural fungicide due to a novel action mode, wide fungicidal spectrum, lower toxicity toward mammalian cells, and environmentally benign characteristics. To discover new strobilurin analogues with high activity against resistant pathogens, a series of new chalcone-based strobilurin derivatives are designed and synthesized by integrating a chalcone scaffold with a strobilurin pharmacophore. The preliminary bioassay showed that some of the chalcone analogues exhibited good in vivo fungicidal activities against Pseudoperoniospora cubensis and Sphaerotheca fuliginea at the dosage of 200 μg mL-1. Two compounds, (￡)-methyl 2-[2-({3-[(￡)-3-(2- chlorophenyl)acryloyl]phenoxy}methyl)phenyl]-3-meth-oxyacrylate (1e) and (E)-methyl 2-[2-({3-[(E)-3-(3-bromophenyl)acryloyl]phenoxy}methyl)phenyl]-3- methoxyacrylate (11), were found to display higher fungicidal activities against P. cubensis (EC90 = 118.52 μg ml-1 for 1e and EC 90 = 113.64 μg mL-1 for 11) than Kresoxim-methyl (EC90 = 154.92 μg mL-1) and were identified as the most promising candidates for further study. The present work demonstrated that strobilurin analogues containing chalcone as a side chain could be used as a lead structure for further developing novel fungicides. To our knowledge, this is the first report about the syntheses and fungicidal activities of chalcone-based strobilurin derivatives.

Synthesis of some pyrazole derivatives and preliminary investigation of their affinity binding to P-glycoprotein

A series of substituted pyrazolines were synthesized and evaluated for their anticancer activity and for their ability to inhibit P-glycoprotein- mediated multidrug resistance by direct binding to a purified protein domain containing an ATP-binding site and a modulator interacting region. Compounds 2a and e have been found to bind to P-glycoprotein with greater affinity.

Synthesis and Selective Inhibitory Activity of 1-Acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole Derivatives against Monoamine Oxidase

A novel series of 1-acetyl-3-(4-hydroxy- and 2,4-dihydroxyphenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole derivatives 1 - 12 have been synthesized and investigated for the ability to selectively inhibit the activity of the A and B isoforms of monoamine oxidase

Antimalarial alkoxylated and hydroxylated chalones: Structure-activity relationship analysis

Chalcones with 2′,3′,4′-trimethoxy, 2′,4′-dimethoxy, 4′-methoxy, 4′-ethoxy, 2′,4′-dihydroxy, and 4′-hydroxy groups on ring B were synthesized and evaluated in vitro against Plasmodium falciparum (K1) in a [3H] hypoxanthine uptake assay. The other ring A was quinoline, pyridine, naphthalene, or phenyl rings with electron-donating or electron-withdrawing substituents of varying lipophilicities. Trimethoxy 6 and 27, dimethoxy 7, 8, 29, and methoxy 31 analogues had good in vitro activities (IC50 5μM). 3-Quinolinyl ring A derivatives were well represented among the active compounds. Hydroxylated chalcones were less active than the corresponding alkoxylated analogues. When evaluated in vivo, 8 and 208 were comparable to chloroquine in extending the lifespan of infected mice. Multivariate data analysis showed that in vitro activity was mainly determined by the properties of ring B. Quantitative structure - activity relationship models with satisfactory predictive ability were obtained for various B ring chalcones using projections to latent structures. A model with good predictability was proposed for 19 active chalcones. Size and hydrophobicity were identified as critical parameters.

Antitumorigenic activities of chalcones. I. Inhibitory effects of chalcone derivatives on 32Pi-incorporation into phospholipids of HeLa cells promoted by 12-O-tetradecanoyl-phorbol 13-acetate (TPA)

More than forty chalcone derivatives were synthesized to examine their structure-activity relationship against tumorigenesis. As a primary screening test, the inhibitory activities of the chalcones for the 32pi-incorporation into phospholipids of HeLa cells enhanced by 12-O-tetradecanoyl-phorbol 13- acetate (TPA) were examined. 3-Hydroxy-chalcone derivatives possessing methyl group in 3'-, 4'-, or 2'-position and isoliquiritigenin homologs showed potent inhibitory activities in the phosphorylation test, which suggests their antitumorigenic effects.

PHOTOREARRANGEMENT OF PHENYL CINNAMATES UNDER MICELLAR ENVIRONMENT

Photolysis of phenyl cinnamates in aqueous SDS medium results in an efficient and high yield synthesis of the corresponding 2'-hydroxychalcones.