15001-27-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3,4-DIMETHOXYBENZYLIDENEACETONE is used as a starting material for the synthesis of various pharmaceuticals and agrochemicals, due to its versatile chemical structure and reactivity.
Used in Cancer Research:
3,4-DIMETHOXYBENZYLIDENEACETONE is used as a cytotoxic agent in cancer research for its potential to target and inhibit the growth of certain cancer cell lines.
Used in Asymmetric Synthesis:
3,4-DIMETHOXYBENZYLIDENEACETONE is used as a reagent in the preparation of chiral catalysts in asymmetric synthesis, contributing to the development of enantioselective reactions and the production of chiral compounds with specific biological activities.
Used in Antioxidant and Anti-inflammatory Research:
3,4-DIMETHOXYBENZYLIDENEACETONE is used in research for its potential antioxidant and anti-inflammatory properties, exploring its applications in the development of therapeutic agents for various diseases and conditions.
Safety Precautions:
Due to its hazardous nature, 3,4-DIMETHOXYBENZYLIDENEACETONE should be handled with care to minimize the risk of skin and eye irritation, as well as potential harmful effects if ingested or inhaled. Proper safety measures, including the use of personal protective equipment and adherence to safety protocols, are essential when working with 3,4-DIMETHOXYBENZYLIDENEACETONE.

InChI:InChI=1/C12H14O3/c1-9(13)4-5-10-6-7-11(14-2)12(8-10)15-3/h4-8H,1-3H3/b5-4+

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 67-64-1 acetone 
• 1080-12-2 Dehydrozingerone 
• 77-78-1 dimethyl sulfate 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 121-33-5 vanillin 
• 74-88-4 methyl iodide 
• 6315-89-5 3,4-dimethoxyaniline 
• 78-94-4 methyl vinyl ketone 
• 67-63-0 isopropyl alcohol 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 52451-39-5 6-(3,4-Dimethoxy-phenyl)-4-ethoxy-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 76539-81-6 6-(3,4-Dimethoxy-phenyl)-4-pyrrolidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-79-2 6-(3,4-Dimethoxy-phenyl)-4-morpholin-4-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-77-0 6-(3,4-Dimethoxy-phenyl)-4-dimethylamino-5,6-dihydro-thiopyran-2-thione 
• 76539-80-5 6-(3,4-Dimethoxy-phenyl)-4-piperidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-78-1 4-Diethylamino-6-(3,4-dimethoxy-phenyl)-5,6-dihydro-thiopyran-2-thione 
• 6302-60-9 4-(3,4-dimethoxy-phenyl)-butan-2-one 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 57507-12-7 5-(3,4-Dimethoxy-phenyl)-3-methyl-pent-1-yn-3-ol 
• 1377071-31-2 (R)-dibenzyl 2-(1-(3,4-dimethoxyphenyl)-3-oxobutyl)malonate 
• 889653-79-6 C₁₂H₁₆O₃ 
• 1443545-65-0 acetic acid (E)-2-acetoxy-4-[5-(3,4-dimethoxyphenyl)-3-oxo-pent-1-enyl]phenyl ester 
• 1443545-71-8 (E)-1-(3,4-dihydroxyphenyl)-5-(3,4-dimethoxyphenyl)-pent-1-en-3-one 
• 1520095-40-2 C₂₁H₃₅⁽²⁾HO₆P⁽¹⁺⁾*C⁽²⁾H₃O^(1-) 

Relevant academic research and scientific papers

One-pot sequential oxidation and aldol-condensation reactions of veratryl alcohol catalyzed by the Ru@ZIF-8 + CuO/basic ionic liquid system

The development of green and efficient methods to transform lignin into fuels and high value-added chemicals is of great importance. In this work, we studied one-pot sequential oxidation and aldol-condensation reactions of veratryl alcohol in a basic ionic liquid (BIL) 1-butyl-3-methylimidazolium 5-nitrobenzimidazolide, which acted as the solvent and provided the basic conditions required for the reactions. The effects of different factors such as the type of catalyst, reaction time, reaction temperature, and the amount of BIL on the oxidation reaction were investigated. It was demonstrated that the catalytic performance of individual Ru@ZIF-8 (zeolitic imidazolate framework-8) or CuO was very poor for the oxidation of veratryl alcohol to veratryl aldehyde. Interestingly, Ru@ZIF-8 + CuO was very efficient for the oxidation reaction and a high yield of veratryl aldehyde could be obtained, indicating the excellent synergistic effect of the two catalysts in the BIL. The veratryl aldehyde generated by the oxidation of veratryl alcohol could react directly with acetone to form 3,4-dimethoxybenzylideneacetone by aldol-condensation reaction catalyzed by the BIL in high yield.

Synthesis, characterization, and reactivity of zinc carboxylate complexes of 2,3-pyridine dicarboxylic acid and (3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl) acetic acid

Ethylenediammonium tris-2,3-pyridine dicarboxylato zinc(II) trihydrate (enH2)2[ZnL3]·2H2O (1) (where H2L = 2,3-pyridine dicarboxylic acid, en = ethylenediamine) and a mixed metal coordination polymer with composition [Na2ZnL′ 3(OAc)(H2O)3]n (2) {where L′ = anion of (3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)acetic acid} are synthesized and characterized. The complex 1 is mono nuclear complex with three coordinating carboxylate anion along with nitrogen chelating zinc ion and there is three uncoordinated carboxylate group one each from three ligand molecules making a complex anion of zinc(II). The zinc(II) ion are in distorted octahedral coordination geometry. In this complex diprotonated ethylenediamines serve as cations. The complex 2 has a polymeric structure with one acetate and three carboxylate of L′ binding to zinc ion provides a tetrahedral environment and these ligands further hold dinuclear units of tri-aquated sodium ions; each dinuclear sodium units are bridged by one water molecule make the coordination polymer. The catalytic ability of these two complexes 1 and 2 towards carbon-carbon bond formation reaction between 3,4-dimethoxy benzaldehyde and acetone are studied. Both the complexes as well as sodium salt of L′ are found to be catalyst for such reactions.

Novel substituted 5-methyl-4-acylaminoisoxazoles as antimitotic agents: Evaluation of selectivity to LNCaP cancer cells

A series of novel antimitotic agents was designed using the replacement of heterocyclic cores in two tubulin-targeting lead molecules with the acylated 4-aminoisoxazole moiety. Target compounds were synthesized via heterocyclization of β-aryl-substituted vinylketones by tert-butyl nitrite in the presence of water as a key step. 4-Methyl-N-[5-methyl-3-(3,4,5-trimethoxyphenyl)isoxazol-4-yl]benzamide (1aa) was found to stimulate partial depolymerization of microtubules of human lung carcinoma A549 cells at a high concentration of 100 μM and to totally inhibit cell growth (IC50 = 0.99 μM) and cell viability (IC50 = 0.271 μM) in the nanomolar to submicromolar concentration range. These data provide evidence of the multitarget profile of the cytotoxic action of compound 1aa. The SAR study demonstrated that the 3,4,5-trimethoxyphenyl residue is the key structural parameter determining the efficiency both towards tubulin and other molecular targets. The cytotoxicity of 3-methyl-N-[5-methyl-3-(3,4,5-trimethoxyphenyl)isoxazol-4-yl]benzamide (1ab) to the androgen-sensitive human prostate adenocarcinoma cancer cell line LNCaP (IC50 = 0.301 μM) was approximately one order of magnitude higher than that to the conditionally normal cells lines WI-26 VA4 (IC50 = 2.26 μM) and human umbilical vein endothelial cells (IC50 = 5.58 μM) and significantly higher than that to primary fibroblasts (IC50 > 75 μM).

Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs

Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.

Synthesis and biological evaluations of monocarbonyl curcumin inspired pyrazole analogues as potential anti-colon cancer agent

Purpose: The monocarbonyl analogs of curcumin (MCACs) have been widely studied for their promising antitumor activity. Pyrazole is a five-membered aromatic heterocyclic system with various bioactivities incorporated frequently in drugs. However, few of MCACs inspired pyrazole analogues were investigated. To search for more potent cytotoxic agents based on MCACs, a series of new 1,5-diaryl/heteroaryl-1,4-pentadien-3-ones inspired pyrazole moiety was synthesized and evaluated on their anti-colon cancer activities. Methods: Fifteen new compounds were synthesized and characterized by spectral datum, and then they were tested preliminarily by MTT assay for their cytotoxic activities against a panel of four human cancer cell lines, namely, gastric (SGC-7901), liver (HepG2), lung (A549), and colon (SW620) cancer cells. Compound 7h exhibited excellent selectivity and outstanding anti-proliferation activity against SW620 cells among these 15 compounds. Further, the mechanisms were investigated by transwell migration and invasion assay, clonogenic assay, cell apoptosis analysis, cell cycle analysis, Western blot analysis. Results: The IC50 value of 7h against SW620 cells was 12 nM, being more potent than curcumin (IC50 = 9.36 μM), adriamysin (IC50 = 3.28 μM) and oxaliplatin (IC50 = 13.33 μM). Further assays showed that 7h inhibited SW620 cell migration, invasion and colony formation obviously, which was due to its ability to induce cell cycle arrest in the G2/M and S phases and apoptosis. Western blot assay revealed that 7h decreased the protein expression of ATM gene, which may primarily contribute to its anticancer activity against SW620 cells. Conclusion: A new MCACs 7h was synthesized and found to exhibit excellent anti-proliferation activity against SW620 cells. Further studies indicated that 7h exerted its anticancer activity against SW620 cells probably via decreasing the ATM protein expression. The present study suggested that 7h was a promising candidate as an anti-colon cancer drug for future development.

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate

A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.

NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENTFORMS OF TAU OLIGOMERS

The present invention relates to novel small molecules of Formulas I, II, III, Ilia, Illb, and IV and pharmaceutically acceptable salts thereof, as well as the preparation and the use thereof.

The construction of novel and efficient hafnium catalysts using naturally existing tannic acid for Meerwein-Ponndorf-Verley reduction

The conversion of carbonyl compounds into alcohols or their derivatives via the catalytic transfer hydrogenation (CTH) process known as Meerwein-Ponndorf-Verley reduction is an important reaction in the reaction chain involved in biomass transformation. The rational design of efficient catalysts using natural and renewable materials is critical for decreasing the catalyst cost and for the sustainable supply of raw materials during catalyst preparation. In this study, a novel hafnium-based catalyst was constructed using naturally existing tannic acid as the ligand. The prepared hafnium-tannic acid (Hf-TA) catalyst was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), and thermogravimetry (TG). Hf-TA was applied in the conversion of furfuraldehyde (FD) to furfuryl alcohol (FA) using isopropanol (2-PrOH) as both the reaction solvent and the hydrogen source. Both preparation conditions and the effects of the reaction parameters on the performance of the catalyst were studied. Under the relatively mild reaction conditions of 70 °C and 3 h, FD (1 mmol) could be converted into FA with a high yield of 99.0%. In addition, the Hf-TA catalyst could be reused at least ten times without a notable decrease in activity and selectivity, indicating its excellent stability. It was proved that Hf-TA could also catalyze the conversion of various carbonyl compounds with different structures. The high efficiency, natural occurrence of tannic acid, and facile preparation process make Hf-TA a potential catalyst for applications in the biomass conversion field.

Dehydrozingerone derivative and preparation method and application thereof

The invention provides a dehydrozingerone derivative as shown in the description. R-R are each independently selected from hydrogen or halogen or a nitro group or an alkyl group or a substitutedalkoxy group or an alkoxy group or a hydroxyl group; the substituent in the substituted alkoxy group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; R and R areeach independently selected from hydrogen or halogen or nitrogen-containing heterocycle; R is selected from an alkyl group or an alkoxy group or a substituted alkoxy group; the substituent in thesubstituted alkyl group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; X is selected from a hetero atom or a hydroxylamine group. The dehydrozingerone derivative hasbroad-spectrum activity against plant pathogenic fungi and bacteria, and has certain nematicidal activity, and is a lead compound with the broad biological activity.