148404-07-3

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 41564-67-4 (E)-1,3-bis(4-methoxyphenyl)-2-propene-1-one 
• 87486-00-8 (E)-4-(3-(4-methoxyphenyl)acryloyl)phenyl acetate 
• 1010118-52-1 C₂₃H₂₀O₅S 
• 126443-12-7 4'-bromo-4-methoxy-trans-chalcone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 

Downstream Products

• 148404-16-4 4-methoxy-4'-(2-pyrrolidinoethoxy) chalkone 
• 148404-10-8 1-(4,5-Dihydro-3-(4-hydroxyphenyl)-5-(4-methoxyphenyl)pyrazol-1-yl)ethanone 
• 370590-08-2 {4-[(E)-3-(4-Methoxy-phenyl)-acryloyl]-phenoxy}-acetic acid ethyl ester 
• 689266-47-5 4'-(2,3-epoxypropoxy)-4-methoxychalcone 

Relevant academic research and scientific papers

Synthesis of 4′-hydroxy-3′-piperidinomethylchalcone derivatives and their cytotoxicity against PC-3 cell lines

A new series of mono Mannich bases of 4′-hydroxychalcones 2a-e carrying a variety of aryl groups was synthesized and the in vitro cytotoxic activities of the new compounds were screened against PC-3 cell lines. Bioactivities of 2a-e, which are reported for the first time in this study, were compared against their precursor 4′-hydroxychalcones 1a-e. Compound 2b was found to be the most potent (IC50 = 3.7 μM) among the compounds synthesized. In addition, the compounds 1a-c and 2d showed moderate cytotoxicity. Incorporation of the 3′-piperidinomethyl group in 1b and 1d raised the potency by 1.68 and 2.19 times respectively and, therefore, seemed to be a noteworthy molecular modification. Correlations were noted between cytotoxicity and one or more physiochemical constants of the aryl ring as well as log P values for the compounds 2a-e. The significant improvement of cytotoxicity of 2b, 2d, and 2e against PC-3 cell lines compared with their chalcone precursors suggests that the incorporation of a piperidinomethyl group is a useful molecular modification and further development of these compounds as candidate cytotoxic agents may be warranted.

From Celecoxib to a Novel Class of Phosphodiesterase 5 Inhibitors: Trisubstituted Pyrazolines as Novel Phosphodiesterase 5 Inhibitors with Extremely High Potency and Phosphodiesterase Isozyme Selectivity

A ligand-based approach involving systematic modifications of a trisubstituted pyrazoline scaffold derived from the COX2 inhibitor, celecoxib, was used to develop novel PDE5 inhibitors. Novel pyrazolines were identified with potent PDE5 inhibitory activit

Chalcone-Supported Cardiac Mesoderm Induction in Human Pluripotent Stem Cells for Heart Muscle Engineering

Human pluripotent stem cells (hPSCs) hold great promise for applications in cell therapy and drug screening in the cardiovascular field. Bone morphogenetic protein 4 (BMP4) is key for early cardiac mesoderm induction in hPSC and subsequent cardiomyocyte derivation. Small-molecular BMP4 mimetics may help to standardize cardiomyocyte derivation from hPSCs. Based on observations that chalcones can stimulate BMP4 signaling pathways, we hypothesized their utility in cardiac mesoderm induction. To test this, we set up a two-tiered screening strategy, (1) for directed differentiation of hPSCs with commercially available chalcones (4’-hydroxychalcone [4’HC] and Isoliquiritigen) and 24 newly synthesized chalcone derivatives, and (2) a functional screen to assess the propensity of the obtained cardiomyocytes to self-organize into contractile engineered human myocardium (EHM). We identified 4’HC, 4-fluoro-4’-methoxychalcone, and 4-fluoro-4’-hydroxychalcone as similarly effective in cardiac mesoderm induction, but only 4’HC as an effective replacement for BMP4 in the derivation of contractile EHM-forming cardiomyocytes.

New class of hybrids based on chalcone and melatonin: a promising therapeutic option for the treatment of colorectal cancer

Considering that conventional chemotherapy provides only a limited increase of overall survival for patients with colorectal cancer (CRC), and resistance is a major cause of therapeutic failure, the emergence of new therapies is needed. Development of dif

Design, Synthesis, and Antimicrobial Evaluation of Novel [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazepine Derivatives

Abstract: The title compounds,3,3′,3″,3′′′-[methylenebis(oxybenzene-5,1,3-triyl)]tetrakis(6,8-diaryl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepines), were synthesized startingfrom dimethyl 4-hydroxyisophthalate which was reacted with dibromomethane toobtain tetramethyl 5,5′-[methylenebis(oxy)]di(benzene-1,3-dicarboxylate). Thelatter was treated with excess hydrazine hydrate, and the resultingtetrahydrazide was converted to tetrakis-1,2,4-triazolyl derivative viacyclization with ethanolic potassium hydroxide, carbon disulfide, and hydrazinehydrate. In the final stage, cyclocondensation with substituted chalconesafforded the target products. The structure of the newly synthesized compoundswas confirmed by elemental analyses and FT-IR and NMR spectra, and theirantimicrobial activities against some bacterial and fungal strains wereestimated by the disc diffusion method.

Efficient solvent- And temperature-tuned access to aldoxime ethers and phenolic functions by Pd-catalyzed C-O cross-coupling of aldoximes with aryl bromides and bromo-chalcones

A single method with a functionality switching option was developed for the first time for the Pd-catalyzed C-O cross-coupling of aryl bromides and bromo-chalcones with aldoximes. The ligand tBuXPhos (L2) was found to be an effective supporting ligand for the Pd-catalyzed coupling of aldoximes with bromo coupling partners. The functionality switching from oxime ethers to a phenolic or hydroxy group was driven by solvent or temperature. This method offers the products in good to excellent yields in short reaction times.

Synthesis and Pharmacological Evaluation of 4-Aryloxyquinazoline Derivatives as Potential Cytotoxic Agents

In the present study, novel 4-aryloxyquinazoline derivatives were synthesized and screened for in vitro cytotoxicity on human cancer cell lines at 10 μM. Some of the synthesized compounds displayed moderate to significant and selective cytotoxic activity

Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones

A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five co

Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR spectroscopy, including COSY and HMQC experiments. Anti-inflammatory activity of the s

Design, Synthesis, and Biological Evaluation of Novel Allosteric Protein Disulfide Isomerase Inhibitors

Protein disulfide isomerase (PDI) is responsible for nascent protein folding in the endoplasmic reticulum (ER) and is critical for glioblastoma survival. To improve the potency of lead PDI inhibitor BAP2 ((E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile), we designed and synthesized 67 analogues. We determined that PDI inhibition relied on the A ring hydroxyl group of the chalcone scaffold and cLogP increase in the sulfonamide chain improved potency. Docking studies revealed that BAP2 and analogues bind to His256 in the b′ domain of PDI, and mutation of His256 to Ala abolishes BAP2 analogue activity. BAP2 and optimized analogue 59 have modest thiol reactivity; however, we propose that PDI inhibition by BAP2 analogues depends on the b′ domain. Importantly, analogues inhibit glioblastoma cell growth, induce ER stress, increase expression of G2M checkpoint proteins, and reduce expression of DNA repair proteins. Cumulatively, our results support inhibition of PDI as a novel strategy to treat glioblastoma.