6876-68-2

Usage

Uses

Used in Pharmaceutical Research:
(2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide is used as a chemical intermediate for the synthesis of pharmaceutical compounds. Its unique molecular structure and functional groups allow it to be a versatile building block in the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry:
(2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide is used as a reagent or starting material in various organic reactions. Its double bond and functional groups enable it to participate in a range of chemical transformations, making it a valuable component in the synthesis of complex organic molecules.
Used in Material Science:
(2E)-N-(4-methylphenyl)-3-phenylprop-2-enamide is used as a component in the development of new materials and compounds for industrial purposes. Its molecular structure and properties can be harnessed to create innovative materials with specific characteristics, such as improved stability, reactivity, or selectivity in various applications.

Upstream product

• 102-92-1 cinnamoyl chloride 
• 106-49-0 p-toluidine 
• 93500-92-6 N-p-tolyl-α,β-dibromohydrocinnamamide 
• 328012-09-5 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylprop-2-en-1-one 
• 621-82-9 Cinnamic acid 
• 90-11-9 1-Bromonaphthalene 
• 1451066-20-8 N-allyl-N-p-tolylcinnamamide 
• 134539-87-0 1-methyl-4-(3-phenyl-1-propen-1-yl)benzene 
• 134539-86-9 1-methyl-4-(3-phenyl-2-propen-1-yl)benzene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 104-55-2 3-phenyl-propenal 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 103-36-6 ethyl 3-phenyl-2-propenoate 

Downstream Products

• 4053-34-3 6-methylquinolin-2(1H)-one 
• 1194653-94-5 (E)-3-benzylidene-5-methylindolin-2-one 
• 4295-11-8 2-chloro-6-methylquinoline 
• 621-79-4 cinnamamide 
• 161332-16-7 1-p-methylphenyl-4(H)-phenyl-2-azetidinone 
• 71231-25-9 N-(4-methylphenyl)-3-phenylpropanamide 

Relevant academic research and scientific papers

Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams

β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method

Design of enamides as new selective monoamine oxidase-B inhibitors

Objectives: To develop of new class of selective and reversible MAO-B inhibitors from enamides. Methods: Syntheses of the titled derivatives (AD1–AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Key findings: Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC50 values of 0.11 and 0.10?μm, respectively, and were followed by AD2 and AD1 (0.51 and 0.71?μm, respectively). Most of the compounds weakly inhibited MAO-A, with the exceptions AD9 and AD7, which had IC50 values of 4.21 and 5.95?μm, respectively. AD3 had the highest selectivity index (SI) value for MAO-B (>363.6) and was followed by AD9 (SI 42.1). AD3 and AD9 were found to be competitive inhibitors of MAO-B with Ki values of 0.044?±?0.0036 and 0.039?±?0.0047?μm, respectively. Reversibility experiments showed AD3 and AD9 were reversible inhibitors of MAO-B; dialysis restored the activity of MAO-B to the reference level. MTT assays revealed AD3 and AD9 were non-toxic to normal VERO cell lines with IC50 values of 153.96 and 194.04?μg/ml, respectively. Computational studies provided hypothetical binding modes for AD3 and AD9 in the binding cavities of MAO-A and MAO-B. Conclusions: These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.

Investigation of anti-inflammatory potential of N-arylcinnamamide derivatives

A series of sixteen ring-substituted N-arylcinnamanilides, previously described as highly antimicrobially effective against a wide spectrum of bacteria and fungi, together with two new derivatives from this group were prepared and characterized. Moreover, the molecular structure of (2E)-N-(2-bromo-5-fluorophenyl)-3-phenylprop-2-enamide as a model compound was determined using single-crystal X-ray analysis. All the compounds were tested for their anti-inflammatory potential, and most tested compounds significantly attenuated the lipopolysaccharide-induced NF-κB activation and were more potent than the parental cinnamic acid. (2E)-N-[2-Chloro-5-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide, (2E)-N-(2,6-dibromophenyl)-3-phenylprop-2-enamide, and (2E)-N-(2,5-dichlorophenyl)-3-phenylprop-2-enamide demonstrated the highest inhibition effect on transcription factor NF-κB at the concentration of 2 μM and showed a similar effectiveness as the reference drug prednisone. Several compounds also decreased the level of TNF-α. Nevertheless, subsequent tests showed that the investigated compounds affect neither IκBα level nor MAPKs activity, which suggests that the N-arylcinnamanilides may have a different mode of action to prednisone. The modification of the C(2,5)0 or C(2,6)0 positions of the anilide core by rather lipophilic and bulky moieties seems to be preferable for the anti-inflammatory potential of these compounds.

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

Ligand- and Additive-Controlled Pd-Catalyzed Aminocarbonylation of Alkynes with Aminophenols: Highly Chemo- and Regioselective Synthesis of α,β-Unsaturated Amides

This work describes the chemo- and regioselective direct aminocarbonylation of alkynes and aminophenols to form hydroxy-substituted α,β-unsaturated amides in good to excellent yields. The latter are valuable compounds in pharmaceuticals and natural products. By a simple choice of different ligands and additives, branched or linear isomers could be selectively formed in excellent regioselectivity. Using a combination of boronic acid and 5-chlorosalicylic acid ( BCSA ) as the additives, linear amides were obtained in high yields and selectivities using 1,2-bis(di-tert-butylphosphinomethyl)benzene (DTBPMB) as the ligand. On the other hand, branched amides could be approached by introducing 1,3-bis(diphenylphosphino)propane as the ligand and p-TsOH·H2O as the additive. In addition to the hydroxyl group, other functional substituents, such as carboxyl and vinyl groups, could also be tolerated using this method. As an application of this strategy, the natural product avenanthramide A could be synthesized directly in 84% yield and in 99% regioselectivity via the carbonylation of 2-amino-5-hydroxybenzoic acid and 4-ethynylphenol. Further studies show that the ligands and the additives are keys to good yields and selectivities.

Cooperation of a Reductant and an Oxidant in One Pot to Synthesize Amides from Nitroarenes and Aldehydes

The reductant zinc powder and the oxidant sodium chlorate were used together in an appropriate ratio in one pot under ambient conditions, to provide an environmentally friendly, effective, and convenient method for the synthesis of aromatic amides in good yields from nitroarenes and aldehydes in the green solvents alcohol and water under atmospheric conditions. The good results indicate that reductants and oxidants with opposing properties can not only be used together without any adverse effects, but also improve the reaction yield through their cooperation.

DDQ-promoted direct transformation of benzyl hydrocarbons to amides via tandem reaction of the CDC reaction and Beckmann rearrangement

An atom-efficient and transition metal-free approach to amides from the corresponding benzyl hydrocarbons through C-H and C-C bond cleavage has been developed. Mechanistic studies have shown that a DDQ-promoted cross-dehydrogenative coupling (CDC) reaction with subsequent oxidation and rearrangement are involved in this transformation. The Royal Society of Chemistry.

Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors

Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.

Tuned C-H functionalization to construct aza-podophyllotoxin/aza- conidendrin derivatives by means of domino cyclization

An efficient domino cyclization method for the construction of aza-podophyllotoxin/aza-conidendrin derivatives has been established. Reactions of different dienes with aryl halides in the presence of a palladium catalytic system produced different kinds of podophyllotoxin derivatives through a highly regioselective C-H functionalization. Treatment of dienes with aryl halides that have electron-withdrawing substituents on the phenyl ring created aza-podophyllotoxin derivatives by means of the functionalization of the C-H bonds ortho to the C-Halide bonds of the incoming aryl halides. The reaction of dienes with 1-iodobenzene or aryl halides that incorporate electron-donating groups produced azaconidendrin derivatives by means of the functionalization of both sp3 C-H and sp2 C-H bonds. The regioselective C-H functionalization for the formation of different pseudo-podophyllotoxin/- conidendrin derivatives is proven by analyses of the 1H NMR spectra of the products and selective X-ray analyses of the structures of the products. Thus the palladium-catalyzed domino cyclization of 1,6-dienes for the preparation of aza-podophyllotoxin/aza-conidendrin derivatives can be controlled by selectively controlling the C-H functionalization.

Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation

A strategy involving palladium-catalysed aromatic C-H functionalisation/ intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl2MeCN 2 and AgOCOCF3, a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield. The Royal Society of Chemistry.