66417-26-3

Usage

Uses

Used in Perfumery Industry:
Methyl 4-Aminocinnamate is used as a fragrance ingredient for its aromatic properties, contributing to the creation of various perfumes and aromatic products.
Used in Sun Protection Products:
In the Cosmetics Industry, Methyl 4-Aminocinnamate is used as an active ingredient in sunscreen and other sun protection products due to its strong UV absorbing capabilities, helping to protect the skin from harmful ultraviolet radiation.
Used in Pharmaceutical Industry:
Methyl 4-Aminocinnamate is used as a pharmaceutical intermediate for its potential medicinal properties, including its anti-inflammatory and antioxidant effects, which are currently being studied for possible applications in drug development.
Used in Skincare Formulations:
In the Skincare Industry, Methyl 4-Aminocinnamate is used as an ingredient in cosmetic formulations for its potential to provide anti-inflammatory and antioxidant benefits, contributing to skin health and protection.

Upstream product

• 637-57-0 p-nitrocinnamic acid methyl ester 
• 292638-85-8 acrylic acid methyl ester 
• 106-40-1 4-bromo-aniline 
• 67-56-1 methanol 
• 17570-30-8 trans-p-aminocinnamic acid 
• 540-37-4 p-aminoiodobenzene 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 106-47-8 4-chloro-aniline 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 34003-15-1 4-(4-phenyl-benzylidenamino)-trans-cinnamic acid methyl ester 
• 35418-07-6 methyl 3-(4-aminophenyl)propionate 
• 501683-21-2 3-{4-[3-(3,4-dimethoxyphenyl)ureido]phenyl}acrylic acid methyl ester 
• 342372-36-5 PX117794 
• 911000-66-3 (E)-3-(4-hydrazino-phenyl)-acrylic acid methyl ester 
• 408368-38-7 methyl (2E)-3-[4-({[4'-(trifluoromethyl)-1,1'-biphenyl-2-yl]carbonyl}amino)phenyl]-2-propenoate 
• 408364-94-3 N-{4-[2-oxo-2-(2-pyridinylamino)ethyl]phenyl}-4'-(trifluoromethyl)-1,1'-biphenyl-2-carboxamide 
• 1310744-74-1 (R,E)-dimethyl 2-(3-(((4-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)amino)methyl)benzamido)pentanedioate 

Relevant academic research and scientific papers

A [2]rotaxane capped by a cyclodextrin and a guest: Formation of supramolecular [2]rotaxane polymer

A [2]rotaxane capped by a β-cyclodextrin and a 2,4,6-trinitrophenyl group has been prepared by dissolving 6-aminocinnamoyl β-cyclodextrin in water with 1-adamantane carboxylic acid and complexation with α-cyclodextrin followed by the reaction with 2,4,6-trinitrobenzene sulfonic acid sodium salt. The [2]rotaxane has been found to form supramolecular polymers by host-guest interactions. Copyright

Synthesis of 2-(N-cyclicamino)quinoline combined with methyl (E)-3-(2/3/4-aminophenyl)acrylates as potential antiparasitic agents

A rationally designed series of 2-(N-cyclicamino)quinolines coupled with methyl (E)-3-(2/3/4-aminophenyl)acrylates was synthesized and subjected to in vitro screening bioassays for potential antiplasmodial and antitrypanosomal activities against a chloroquine-sensitive (3D7) strain of Plasmodium falciparum and nagana Trypanosoma brucei brucei 427, respectively. Substituent effects on activity were evaluated; meta-acrylate 24 and the ortho-acrylate 29 exhibited the highest antiplasmodial (IC50 = 1.4 μM) and antitrypanosomal (IC50 = 10.4 μM) activities, respectively. The activity against HeLa cells showed that the synthesized analogs are not cytotoxic at the maximum tested concentration. The ADME (absorption, distribution, metabolism, and excretion) drug-like properties of the synthesized compounds were predicted through the SwissADME software.

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells

In order to get a better insight into the relationship between molecular structure and photovoltaic performance, six monoazo dye molecules containing benzoic and cinnamic acid moieties were synthesized and their photovoltaic properties were studied. Three of them have not been previously used in solar cells. Spectroscopic measurements of the investigated compounds coupled with theoretical calculations were performed. Short-circuit current density, open-circuit voltage, and fill-factor were determined. It was found that a larger amount of short-circuit current density will be generated if the HOMO–LUMO energy gap is lower, determined by the stability of the molecule and the electronic effect of the donor moiety. Among both series of synthesized dye molecules, the highest obtained values of short-circuit current density were achieved with (2-hydroxynaphthalene-1-ylazo)benzoic acid and (2-hydroxynaphthalene-1-ylazo)cinnamic acid, and thus they were regarded as promising candidates for application in dye-sensitized solar cells.

Pd–Schiff base complex supported on Fe3O4 magnetic nanoparticles: A new and highly efficient reusable catalyst for C–C bond formation in water

A protocol is introduced for the preparation of a new cage-like Pd–Schiff base organometallic complex supported on Fe3O4 nanoparticles (Fe3O4@Schiff-base-Pd). The structure of the nanomagnetic catalyst was comprehensively characterized using Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy, Brunauer–Emmett–Teller measurements, scanning electron microscopy (SEM), transmission electron microscopy, X-ray mapping, thermogravimetric analysis, vibrating sample magnetometry and inductively coupled plasma atomic emission spectroscopy. In the second stage, the catalytic activity of this catalyst was studied in the Suzuki and Heck cross-coupling reactions in water as a green solvent. In this sense, simple preparation of the catalyst from commercially available materials, high catalytic activity, simple operation, short reaction times, high yields and use of green solvent are some advantages of this protocol. Finally, the nanocatalyst was easily recovered, using an external magnet, and reused several times without significant loss of its catalytic efficiency. In addition, the stability of the catalyst after recycling was confirmed using SEM, XRD and FT-IR techniques.

Synthesis and Catalytic Applications of [N,N]-Pyrrole Ligands for the Regioselective Synthesis of Styrene Derivatives

We report the synthesis of two [N,N]-donor ligands (5 a–b) containing a 2-chalcogenazoline as the structural motif. These compounds were synthesized from a common intermediate Fischer type aminocarbene complex (3). The palladium-complexes of these [N,N]-donor ligands were successfully used as catalytic precursors in the Mizoroki-Heck coupling reaction between aryl halides and methyl acrylate, styrene and ethylene. For methyl acrylates, high yields with TOF values between 0.6 and 5.5×105 h?1 were obtained. In the case of ethylene, we reached high regioselectivities to obtain a diversity of styrene derivatives under soft pressure conditions, with good values of TON and TOF. (Figure presented.).

Fe3O4@Boehmite-NH2-CoII NPs: An inexpensive and highly efficient heterogeneous magnetic nanocatalyst for the Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions

Herein we report the synthesis of a magnetically separable core-shell-like Fe3O4@Boehmite-NH2-CoII NPs as an environmentally friendly heterogeneous catalyst. The as-prepared nanocatalyst was well characterized by various techniques such as FT-IR, XRD, BET, TEM, FE-SEM, EDX, TGA, H2-TPR, VSM, ICP-OES and elemental analysis and evaluated for the Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions in a green solvent (H2O). The results of characterization studies revealed the superparamagnetic behavior of the Fe3O4 NP core encapsulated by a Boehmite NP shell. Also, it was clearly found that the size of the particles was about 13-54 nm. In comparison with previously reported catalysts, Fe3O4@Boehmite-NH2-CoII NPs exhibited perfect catalytic efficiency for the Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions under mild conditions without using toxic solvents. The concerted effects between individual components of the catalyst and also its unique egg-like nanostructure led to the high catalytic performance of Fe3O4@Boehmite-NH2-CoII NPs. Also, the introduction of Co significantly lowers the cost of the catalyst. More importantly, the longevity of the nanocatalyst was studied and it was found that the magnetic nanocatalyst was stable under the reaction conditions and could be easily reused for at least seven consecutive cycles without a discernible decrease in its catalytic activity or metal leaching.

Design and Synthesis of Ligand Efficient Dual Inhibitors of Janus Kinase (JAK) and Histone Deacetylase (HDAC) Based on Ruxolitinib and Vorinostat

Concomitant inhibition of multiple oncogenic pathways is a desirable goal in cancer therapy. To achieve such an outcome with a single molecule would simplify treatment regimes. Herein the core features of ruxolitinib (1), a marketed JAK1/2 inhibitor, have been merged with the HDAC inhibitor vorinostat (2), leading to new molecules that are bispecific targeted JAK/HDAC inhibitors. A preferred pyrazole substituted pyrrolopyrimidine, 24, inhibits JAK1 and HDACs 1, 2, 3, 6, and 10 with IC50 values of less than 20 nM, is 100 nM potent against JAK2 and HDAC11, and is selective for the JAK family against a panel of 97 kinases. Broad cellular antiproliferative potency of 24 is supported by demonstration of JAK-STAT and HDAC pathway blockade in hematological cell lines. Methyl analogue 45 has an even more selective profile. This study provides new leads for assessment of JAK and HDAC pathway dual inhibiton achieved with a single molecule.

Pd0.09Ce0.91O2-Δ: A sustainable ionic solid-solution precatalyst for heterogeneous, ligand free Heck coupling reactions

A quick and easy method for the preparation of Pd2+ metal ion substituted in ceria, Pd0.09Ce0.91O2-δ solid solution oxide, is described. The Pd0.09Ce0.91O2-δ solid solution oxide was fully characterized by XRD, ICP-OES, BET, XPS, SEM, EDX, TEM, TGA and Raman spectroscopy. All characterization techniques strongly suggested that Pd2+ was successfully incorporated into the lattice structure of ceria. The effect of the reaction conditions on the catalytic properties of the Pd0.09Ce0.91O2-δ solid solution catalyst initially was studied in detail with the model Heck reaction of iodobenzene and methylacrylate to obtain optimum reaction conditions. The Pd0.09Ce0.91O2-δ solid solution catalyst then afforded substituted alkenes in good to excellent yields under these optimum reaction conditions. Steric and electronic effects were also studied, and were found to influence the catalytic activity. Characterization of the used catalyst suggests that Pd2+ in Pd0.09Ce0.91O2-δ is reduced in situ to Pd0 when employed in the Heck cross-coupling reactions. The catalyst was easily recovered by centrifuge and reused three times without significant loss of catalytic efficiency.

Arylhydrazones Derivatives Containing a Benzothiazole Moiety, Efficient Ligands in the Palladium-Catalyzed Mizoroki–Heck and Suzuki–Miyaura Cross-coupling Reactions under IR Irradiation

A simple arylhydrazone containing the benzothiazole moiety which may be used as an efficient ligand in the palladium-catalyzed Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions, under infrared irradiation as an alternative source of energy, is presented. The reactions proceeded with extremely high efficiency under mild conditions and produced very good yields.

Synthesis and evaluation of substituted 4-(N-benzylamino)cinnamate esters as potential anti-cancer agents and HIV-1 integrase inhibitors

Encouraging selectivity and low micromolar activity against HeLa cervical carcinoma (IC50? 3.0 μM) and the aggressive MDA-MB-231 triple negative breast carcinoma (IC50? 9.6 μM) cell lines has been exhibited by a number of readily acc