19039-94-2

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 67-64-1 acetone 
• 1963-36-6 4-methoxycinnamaldehyde 
• 1896-62-4 (E)-benzalacetone 
• 78-94-4 methyl vinyl ketone 
• 2236-01-3 acetonyltriphenylphosphonium bromide 

Downstream Products

• 19142-33-7 all-trans-Bis-(α-methyl-3,4,5-trimethoxycinnamyliden)-hydrazin 
• 103976-89-2 C₁₄H₁₉N₃O₃S 
• 196957-41-2 Trimethyl-[(E)-1-methylene-3-(3,4,5-trimethoxy-phenyl)-allyloxy]-silane 
• 196957-42-3 (E)-3-tert-butyldimethylsiloxy-1-(3,4,5-trimethoxyphenyl)-1,3-butadiene 
• 196957-43-4 Triisopropyl-[(E)-1-methylene-3-(3,4,5-trimethoxy-phenyl)-allyloxy]-silane 
• 1217503-53-1 (1E,4E)-1-(3-(1-ethoxyethoxy)phenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 
• 1217503-50-8 (1E,4E)-1-(2,4,5-trimethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 
• 1217503-47-3 (1E,4E)-1-phenyl-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 
• 1217503-54-2 (1E,4E)-1-(3-chlorophenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 
• 1443780-50-4 4-phenyl-4-(3,4,5-trimethoxyphenyl)butan-2-one 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 30273-57-5 (E)-tert-butyl 3-(3,4,5-trimethoxyphenyl)acrylate 

Relevant academic research and scientific papers

3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: A novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity

This study revealed that various alicyclic and acyclic compounds containing the 3-(3,4,5-trimethoxyphenyl)-2-propenoyl group displayed potent MDR reversal properties. In particular, a concentration of 4 μg/ml of 2,5-bis(3,4,5-trimethoxyphenylmethylene)cyc

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.

Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones

The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.

Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives

In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.

Thermal decarboxylative Nazarov cyclization of cyclic enol carbonates involving chirality transfer

Decarboxylative Nazarov cyclization of chiral cyclic enol carbonates proceeded to afford chiral 2-cyclopentenones with excellent chirality transfer under thermal conditions without any catalyst. Interestingly, the thermal decarboxylative Nazarov cyclization furnished the desired product with better chirality transfer than the Lewis acid-catalyzed reaction.

Method for synthesizing asymmetrical mono-carbonyl curcumin analogue intermediate

The invention discloses a method for synthesizing an asymmetrical mono-carbonyl curcumin analogue intermediate. The method comprises the following steps: using one of acetone, cyclopentanone, cyclohexanone, pyrone and 4-piperidone and benzaldehyde with a substituent group as reaction raw materials, using anhydrous dimethyl sulfoxide as a solvent, firstly reacting for 48 h under the catalysis of L-proline, then using concentrated hydrochloric acid to provide an acidic condition for dehydration, and carrying out room temperature reaction synthesis to obtain the asymmetrical mono-carbonyl curcumin analogue intermediate. All kinds of raw materials used in the method are generally commercialized, and can be directly purchased and obtained. Compared with the prior art, a great number of solid wastes cannot be generated without using any precious metal catalyst or halogenated solvent. Therefore, the method has the advantages of simple steps, easy operation, little pollution, high yield, easyobtaining for raw materials and the like, and has potential and wide application prospects, so that reference can be provided for the synthesis of the asymmetrical mono-carbonyl curcumin analogue intermediate.

Novel Benzo[a]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis

Paraptosis is nonapoptotic cell death characterized by massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability to induce cytoplasmic vacuolation were analyzed. Structural optimization led to the identification of the potent compound 22b, which inhibited cancer cell proliferation in vitro and in vivo and profoundly facilitated paraptosis-like cell death and induced caspase-dependent apoptosis. Further investigation revealed that 22b-mediated vacuolation originated from persistent ER stress and upregulation of LC3B. Paraptosis induced by benzo[a]quinolizidine derivatives thus represents an alternative strategy for cancer chemotherapy.

Palladium-catalyzed conjugate addition of arylsulfonyl hydrazides to α,β-unsaturated ketones

A palladium-catalyzed desulfitative-denitrogenative conjugate addition of arylsulfonyl hydrazides to α,β-unsaturated ketones is described. The reaction showed very good selectivity and tolerated a wide range of functionalities under an atmosphere of oxygen with or without the aid of a metal co-oxidant. The Royal Society of Chemistry 2013.

Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues

The present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the α,β-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these α,β-unsaturated styryl lactones, thereby further focusing the design of novel candidates.

Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway

A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-κB inhibition activity over the parent compound curcumin, at least in part by inhibiting IκB phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.