127034-55-3

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 98-86-2 acetophenone 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 1082730-34-4 (E)-N-methoxy-N-methyl-3-(3,4,5-trimethoxyphenyl)acrylamide 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 201230-82-2 carbon monoxide 
• 477727-72-3 3,4,5-trimethoxy-β-iodostyrene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 143505-05-9 5,6-Dihydro-1,3-dimethyl-7-phenyl-6-(3-phenyl-1-(3,4,5-trimethoxyphenyl)-3-oxoprop-1-yl)-5-(3,4,5-trimethoxyphenyl)-pyrido<2,3-d>pyrimidin-2,4-(1H,3H)-dion 
• 105686-78-0 2-(4-Chloro-phenyl)-6-phenyl-4-(3,4,5-trimethoxy-phenyl)-pyridine 
• 105686-76-8 2,6-diphenyl-4-(3,4,5-trimethoxyphenyl)pyridine 
• 105701-01-7 2-Phenyl-6-p-tolyl-4-(3,4,5-trimethoxy-phenyl)-pyridine 
• 1206190-36-4 3-phenyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide 
• 655231-67-7 1-acetyl-5-(3,4,5-trimethoxyphenyl)-3-phenyl-4,5-dihydro-(1H)-pyrazole 
• 1296863-64-3 4,4,4-tribromo-3-(3,4,5-trimethoxyphenyl)-1-phenylbutan-1-one 
• 1296863-78-9 2,2-diethoxy-3-(3,4,5-trimethoxyphenyl)-5-phenyl-2,3-dihydrofuran 
• 1296863-85-8 ethyl 2-(3,4,5-trimethoxyphenyl)-4-oxo-4-phenylbutanoate 
• 1415466-08-8 5,6,7-trimethoxy-2-phenyl-3,3a-dihydropyrazolo[5,1-a]isoindol-8-one 
• 1448042-17-8 1-(3,4,5-trimethoxy-phenyl)-3-phenyl-hexa-1,5-dien-3-ol 
• 1277171-24-0 C₂₉H₂₈N₄O₄S 

Relevant academic research and scientific papers

Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration

The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.

Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones

Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).

Triarylpyrazole Derivatives as Potent Cytotoxic Agents; Synthesis and Bioactivity Evaluation Pyrazole Derivatives as Anticancer Agent

Background During the last recent years, several anti-cancer agents were introduced for the treatment of diverse kinds of cancer. Despite their potential in the treatment of cancer, drug resistance and adverse toxicity such as peripheral neuropathy are so

Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions

A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.

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.

Effect of substituents in the A and B rings of chalcones on antiparasite activity

Chalcones are a group of natural products with many recognized biological activities, including antiparasitic activity. Although a lot of chalcones have been synthetized and assayed against parasites, the number of structural features known to be involved in this biological property is small. Thus, in the present study, 21 chalcones were synthesized to determine the effect of substituents in the A and B rings on the activity against Leishmania braziliensis, Trypanosoma cruzi, and Plasmodium falciparum. The compounds were active against L. braziliensis in a structure-dependent manner. Only one compound was very active against T. cruzi, but none of them had a significant antiplasmodial activity. The electron-donating substituents in ring B and the hydrogen bonds at C-2′ with carbonyl affect the antiparasitic activity.

Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles

In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.

Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds

A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.

Discovery of novel chalcone-dithiocarbamates as ROS-mediated apoptosis inducers by inhibiting catalase

Novel chalcone-dithiocarbamate hybrids were designed, synthesized and evaluated for antiproliferative activity against selected cancer cell lines (MGC803, MCF7, and PC3). Among these analogues, (E)-2-oxo-2-((4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)am

A class of novel tubulin polymerization inhibitors exert effective anti-tumor activity via mitotic catastrophe

In current work, a class of novel 4,5-dihydro-1H-pyrazole-1-carboxylate derivatives (E01-E28) were designed, synthesized and evaluated. Among them, the most potent compound E24 exhibited comparable activity against a panel of cancer cells (GI50