2657-25-2

Usage

Uses

Used in Antineoplastic Applications:
4'-HYDROXYCHALCONE is used as an antineoplastic agent for its ability to inhibit the growth of various cancer cell lines, such as K562, U937, and Jurkat, in a dose-dependent manner without affecting the viability of peripheral blood mononuclear cells (PBMCs).
Used in Antiviral Applications:
In the field of virology, 4'-HYDROXYCHALCONE is used as an antiviral agent for its moderate to good activity against the tobacco mosaic virus (TMV).
Used in Pharmaceutical Industry:
4'-HYDROXYCHALCONE is used as a compound with potential applications in drug development for its ability to inhibit TNF-α-induced NF-κB signaling and the trypsin-, chymotrypsin-, and caspase-like proteolytic activities of the 26S proteasome in K562 cells in a dose-dependent manner. Additionally, it exhibits inhibitory effects on glutathione reductase (GSH-RD; IC50 = 47.3 μM) in vitro in a reversible and non-competitive manner.

Upstream product

• 100-52-7 benzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 140-10-3 (E)-3-phenylacrylic acid 
• 108-95-2 phenol 
• 468060-22-2 4-(tetrahydropyran-2-yloxy)chalcone 
• 85699-00-9 1-[4-(methoxymethoxy)phenyl]-1-ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 98-86-2 acetophenone 
• 2757-04-2 phenyl cinnamate 
• 102-92-1 cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 364333-61-9 C₂₀H₂₀O₃ 
• 22966-19-4 trans-4'-methoxychalcone 

Downstream Products

• 102692-58-0 (Z)-4'-hydroxychalcone 
• 252006-56-7 1-(3-(4-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone 
• 252006-47-6 (2E,2'E)-1,1'-((propane-1,3-diylbis(oxy))bis(4,1-phenylene))bis(3-phenylprop-2-en-1-one) 
• 252006-48-7 1,4-bis(4-cinnamoylphenoxy)butane 
• 370590-07-1 ethyl {4-[(2E)-3-phenylprop-2-enoyl]phenoxy}acetate 
• 64820-41-3 4-(2-phenyl-2,3-dihydrobenzo[b][1,4]thiazepine-4-yl)phenol 
• 1093881-86-7 1-(4-hydroxyphenyl)-4-nitro-3-phenylbutan-1-one 
• 1021427-81-5 2-(4-hydroxybenzoyl)-6,6-dimethyl-3-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 

Relevant academic research and scientific papers

Near-infrared fluorescent probe for evaluating the acetylcholinesterase effect in the aging process and dietary restrictionviafluorescence imaging

Dietary restriction (DR), as a natural intervention, not only benefits the neuroendocrine system, but also has an antiaging action. Acetylcholinesterase (AChE) is one of the most important bioactive substances and plays a major part in choline changes in the aging process. Thus, we aim to evaluate the effect of DR on AChE in the brains of aging animals. In this study, we synthesize a NIR fluorescent probe BD-AChE for the real-time andin situmonitoring of AChE level changes in living cells and living mice, notably in brains.In situvisualization with BD-AChE verified a decrease in the AchE level in the brains of mice aging models. Evidently, the prepared probe has the excellent capability of measuring AChE variation in the brains of aging mice with DRviaNIR fluorescence bioimaging, indicating that long-term DR can effectively affect AChE levels in the brain. The attenuation of AChE level in the brain of aging mice after DR could be helpful in infering the advantageous impact of DR on age-related neurodegenerative disease, as a better treatment alternative in the future.

Efficient electron transporting and panchromatic absorbing FRET cassettes based on aza-BODIPY and perylenediimide towards multiple metal FRET-Off sensing and ratiometric temperature sensing

Multichromophoric triads 1 and 2 based on aza-BODIPY as the central chromophore and bay-substituted (tetrachloro- and tetraphenoxy-)perylenediimides (PDI) as peripheral chromophores have been designed and synthesized that are panchromatic absorbers and near infrared (NIR) emitters. Both triads 1 and 2 exhibited ～99% F?rster resonance energy transfer (FRET) from the peripheral PDIs to central aza-BODIPY. The excitation energy transfer from PDI to aza-BODIPY was studied via steady state emission, fluorescence quantum yield, time resolved fluorescence emission and theoretical calculations. These studies revealed quantitative singlet excitation energy transfer efficiencies for 1 and 2. Electrochemical studies revealed the strong electron deficient character of these triads and thus electron mobilities of these triads were measured using space charge limited current (SCLC) method. Triads 1 and 2 exhibited appreciable electron mobilities of 2.44 ± 1.70 × 10-3 cm2 V-1 s-1 and 4.00 ± 1.50 × 10-3 cm2 V-1 s-1 respectively, an order of magnitude higher mobility than aza-BODIPY based small molecules reported in the literature. Leveraging upon the dual emission behaviour of these triads, ratiometric FRET sensing as well as ratiometric temperature sensing behaviour were investigated via steady state absorption and fluorescence measurements. Triads 1 and 2 showed remarkable ratiometric FRET-off sensing where the addition of metals such as Co2+ and Fe3+ led to near-quantitative FRET off for both the triads. Triads 1 and 2 also serve as efficient ratiometric temperature sensors with positive temperature coefficients and small temperature sensitivities of ～0.29% °C-1 and ～0.14% °C-1 respectively that suggest the possibility of precise physiological temperature measurements using these triads.

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women’s cancer cells

Curcumin and cinnamaldehyde are natural products whose antineoplastic activity has been well explored in biological evaluations. However, their poor chemical stability under physiological conditions has been an obstacle to their use as therapeutic agents. Herein, we designed and synthesized two series of curcumin-cinnamaldehyde hybrids by removing reactive functionalities, including β-diketone and aldoxyl moieties. All compounds were evaluated by the MTT assay to determine their antiproliferative activity against women’s cancer cells. Compound 5a (3′-hydroxychalcone) demonstrated potent antiproliferative activity against all cancer cell lines tested, with IC50 values ranging from 2.7 to 36.5 μM. Compound 5a was more active and selective than curcumin and cinnamaldehyde (parent compounds) against the CaSki, SiHa, C33, and A431 cell lines, displaying a higher selectivity index (SI = 8.5) than curcumin (SI = 0.8) toward the non-tumorigenic HaCaT cell line. Clonogenic experiments indicated that compound 5a inhibited A431 colony formation in a concentration-dependent manner. In addition, 5a was more stable than its parent compounds in pH 7.4 at 37 °C. In silico investigations suggested that 5a has good drug-likeness properties. In conclusion, our results indicate the use of curcumin and cinnamaldehyde as parent compounds for the design of hybrids with attractive antiproliferative activity and chemical stability.

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

Polymethine-Based Semiconducting Polymer Dots with Narrow-Band Emission and Absorption/Emission Maxima at NIR-II for Bioimaging

Deep-penetration fluorescence imaging in the second near-infrared (NIR-II) window heralds a new era of clinical surgery, in which high-resolution vascular/lymphatic anatomy and detailed cancerous tissues can be visualized in real time. Described here is a series of polymethine-based semiconducting polymers with intrinsic emission maxima in the NIR-IIa (1300–1400 nm) window and absorption maxima ranging from 1082 to 1290 nm. These polymers were prepared as semiconducting polymer dots (Pdots) in aqueous solutions with fluorescence quantum yields of 0.05–0.18 %, and they demonstrate promising applications in noninvasive through-skull brain imaging in live mice with remarkable spatial resolution as well as signal-to-background contrast. This study offers a platform for future design of NIR-IIa or even NIR-IIb emitting Pdots.

C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range

Abstract: To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones (15–36 and 37–41) and structurally related compounds (42–47) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10?μM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (Ki (r) = 1.6?μM). The structure–affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38—that contains an α,?-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract: C3 amino-substituted chalcone derivative (38) with C3′ Br substitution on benzylidene ring B possesses selective adenosine rA1 receptor affinity in micromolar range.[Figure not available: see fulltext.]

Synthesis and anticancer activity of chalcone–quinoxalin conjugates

Two series of quinoxaline–chalcone conjugates have been prepared by aldolic condensation and aromatic nucleophilic substitution reaction, and their anticancer activity against three cancer cell lines including benign prostatic hyperplasia epithelial cell (BPH-1), neuron-like rat pheochromocytoma cell line (PC12) and human breast cancer cell line (MCF-7) were evaluated in?vitro. All of the synthesized compounds exhibited moderate to good activity against the cancer cell lines selected. Particularly, Compound A5 showed the excellent potent activity against BPH-1 and MCF-7 with IC50 values of 10.4 and 9.1 μM, respectively, which is similar to doxorubicin (14.1 and 9.2 μM, respectively). As well as compound B6 exhibited most excellent activity toward PC12 with IC50 values of 16.4 μM. Compound A10 exhibited 55.4, 36.8 and 54.5 folds higher selectivity for BPH-1, PC12 and MCF-7 cells than for HEK-293 cell, respectively. In addition, theoretical biological activities of compounds A5 and A10 were evaluated by SwissADME.

Silica-supported heterogeneous catalysts-mediated synthesis of chalcones as potent urease inhibitors: in vitro and molecular docking studies

Abstract: We herein report a facile and high yielding protocol for silica-supported heterogeneous catalysts-mediated synthesis of chalcones. A comparison of results of our synthesis with conventional synthetic protocols is also being offered to assess the efficiency of the prepared catalysts. Biological evaluation of the newly synthesized compounds as urease inhibitors was performed. Most of the compounds were found to have potent urease inhibition activity. The chalcone 3-(3-hydroxyphenyl)-1-phenylpropenone was found to be the most potent with percentage inhibition 86.17 ± 0.89 and half maximal inhibitory concentration (IC50) value 11.51 ± 0.03 μM. The molecular docking study emphasized that the same congeners 3-(furan-2-yl)-1-(4-hydroxyphenyl)propenone, 3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)propanone, and 3-[4-(dimethylamino)phenyl]-1-(p-tolyl)propenone showed very good inhibitory potential against urease and show a higher docking scores 5718, 5940, 5596 and an ACE of ? 246.66, ? 244.79, and ? 243.06 kJ/mol, respectively than the control ligand. Graphic abstract: [Figure not available: see fulltext.].

Near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, preparation method and application thereof

The invention discloses a near-infrared II thiapyran salt fluorescent compound capable of targeting mitochondria, a preparation method and application thereof. According to the invention, a thiapyransalt heterocyclic structure is modified, different modification groups are introduced, and the emission wavelength of the thiapyran salt heterocyclic structure can be redshifted to a near-infrared IIregion (1000-1200 nm); the compound has good light stability, is easy for post-modification, can be connected with different biomarkers (polypeptide, antibody, PEG, folic acid and the like) through chemical bonding, improves the water solubility and targeting property, reduces the biotoxicity, and improves the bioavailability; and the compound can be used for mitochondrial imaging, drug efficacy evaluation, solid tumor imaging for breast cancer, osteosarcoma, glioma and other solid tumors, and vascular imaging, can also be used for surgical navigation, early diagnosis of diseases, intraoperative real-time monitoring, photothermal therapy, photodynamic therapy and other biological applications, and has good industrial production values and biomedical application prospects.