4087-66-5

Upstream product

• 100-52-7 benzaldehyde 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 91-16-7 1,2-dimethoxybenzene 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 4732-70-1 3,4-dimethoxyphenylglyoxylic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 536-74-3 phenylacetylene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 100-42-5 styrene 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 

Downstream Products

• 4087-68-7 5,6-dimethoxy-3-phenyl-2,3-dihydro-1H-inden-1-one 
• 49747-52-6 1-(3,4-dimethoxyphenyl)-3-phenylpropan-1-one 
• 49747-61-7 1-(3,4-dimethoxy-phenyl)-3-morpholin-4-yl-3-phenyl-propan-1-one 
• 141075-46-9 7,7-dimethyl-5-oxo-2-(3',4'-dimethoxyphenyl)-4-phenyl-5,6,7,8-tetrahydro-4H-1-benzopyran 
• 1449465-02-4 7-(3,4-dimethoxyphenyl)-4-methoxy-2-methylsulfanyl-5-phenyl-7H-thiopyrano[2,3-d]pyrimidine 
• 1449464-82-7 (E)-1-[4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidin-5-yl]-3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-ol 
• 49747-86-6 1-(3,4-dimethoxy-phenyl)-3-morpholin-4-yl-3-phenyl-propan-1-ol 
• 908254-37-5 ethyl 6-phenyl-4-(3,4-dimethoxyphenyl)-4-(trimethylsiloxy)-(5E)-hexen-2-ynoate 

Relevant academic research and scientific papers

Dynamic-Reversible Photoacoustic Probe for Continuous Ratiometric Sensing and Imaging of Redox Status in Vivo

Here, we report a reversible photoacoustic (PA) probe, BDP-DOH, to image the localized redox state in vivo via monitoring the dynamic changes of the redox couple, superoxide anion (O2a￠-) and glutathione (GSH). The probe features a s

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.

Discovery of N-pyridoyl-Δ2-pyrazolines as Hsp90 inhibitors

Hsp90, as a key molecular chaperone, plays an important role in modulating the activity of many cell signaling proteins and is an attractive target for anticancer therapeutics. Herein, we report the discovery of N-pyridoyl-Δ2-pyrazoline analogs

DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives

A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.

Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones

A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.

Synthesis and evaluation of central antinociceptive activity of ring substituted chalcones; molecular docking studies with monoacylglycerol lipase (MAGL) enzyme

Chalcones possess Michael acceptor property due to the presence of α,β-unsaturated enone moiety in their structure. In the present study, molecular docking was performed to predict binding affinity of ring substituted chalcones with Monoacylglycerol lipase (MAGL), a serine hydrolase enzyme which can inhibited by Michael acceptors such as maleimide derivatives. 3, 4-Dimethoxy derivative, 3 h with -44.45 kJmol-1 of interaction energy, exhibited highest binding affinity and formed Pi-Sulphur interactions with methionine-123 residue of MAGL enzyme. As MAGL is an emerging target for antinociceptive drug development, ring substituted chalcones were synthesized and evaluated for their central antinociceptive activity using tail immersion and hot plate methods. The results revealed that compound 3 h chalcone bearing methoxy groups at 3rd and 4th positions of phenyl ring exhibited good antinociceptive activity in both the models. Good correlation was observed between antinociceptive activity and binding affinity toward MAGL in case of compound 3 hour.

Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls

The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.

Discovery of potent cytotoxic ortho-aryl chalcones as new scaffold targeting tubulin and mitosis with affinity-based fluorescence

A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.

NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER

Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.

CHALCONE DERIVATIVES AS NRF2 ACTIVATORS

Compounds and methods for treating or preventing a disease, disorder or condition associated with an Nrf2-regulated pathway, including those associated with an autoimmune disease, comorbidity associated with diabetes, such as retinopathy and nephropathy, bone marrow transplant for leukemia and related cancers, bone marrow deficiencies, inborn errors of metabolism, and other immune disorders, oxidative stress, respiratory infection, ischemia, neurodegenerative disorders, radiation injury, neutropenia caused by chemotherapy, autoimmunity, and congenital neutropenic disorders, and for restoring a corticosteroid responsiveness, in a subject are provided.