13026-23-8

Usage

Uses

4-Phenylcinnamic acid is used as pharmaceutical intermediates and for chemical research.

InChI:InChI=1/C15H12O2/c16-15(17)11-8-12-6-9-14(10-7-12)13-4-2-1-3-5-13/h1-11H,(H,16,17)/b11-8+

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 98-80-6 phenylboronic acid 
• 108-24-7 acetic anhydride 
• 3218-36-8 4-Phenylbenzaldehyde 
• 141-78-6 ethyl acetate 
• 113538-22-0 (E)-3-([1,1′-biphenyl]-4-yl)acrylaldehyde 
• 20883-99-2 methyl (E)-3-([1′,1′′-biphenyl]-4′-yl)acrylate 
• 124-38-9 carbon dioxide 
• 29079-00-3 4-ethynyl-1,1'-biphenyl 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 108-86-1 bromobenzene 
• 159896-15-8 trans-4-(2-carboxyethenyl)benzeneboronic acid 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 1393590-23-2 phenyl (E)-3-(biphenyl-4-yl)acryloylsulfamate 
• 1430417-12-1 (E)-1-(allyloxy)-3-(3,4-dimethoxyphenyl)-1-oxopropan-2-yl 3-(4-phenylphenyl)acrylate 
• 155760-02-4 (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid 
• 170080-13-4 ([1,1’-biphenyl]-4-yl)alanine 
• 2350-89-2 p-vinylbiphenyl 
• 40231-42-3 4-(1-phenylvinyl)-1,1′-biphenyl 
• 859505-62-7 C₂₄H₂₀O₅ 
• 859505-70-7 C₂₁H₁₄O₅ 
• 1363436-46-7 N-[2-(4-Biphenyl-4-ylethynyl-phenyl)-1-methyl-ethyl]acetamide 
• 32340-38-8 biphenyl-4-yl-propynoic acid 

Relevant academic research and scientific papers

Intramolecular Electron Transfer and SN2 Reactions in the Radical Anions of 1-(4-Biphenylyl)-ω-haloalkane Studied by Pulse Radiolysis

One-electron reduction of 1-(4-biphenylyl)-ω-haloalkane (BPX-n) by solvated electrons and the intramolecular reactions of the radical anion thus formed have been investigated using the pulse-radiolysis technique.The spectrum observed immediately after the pulse has an absorption maximum at 410 nm which is assigned to the corresponding biphenyl radical anion.The decay behavior of all these 410-nm bands follows first-order kinetics and the rates are dependent on the methylene chain length, n.With BPCl-0 and BPCl-2, which provide large rate constants (7.5E7 and 1.7E8 s-1, respectively) and large G values of 4-alkylbiphenyl formation, an intramolecular electron transfer from a biphenyl radical anion to a C-Cl bond is presumed.The rate constants of the radical anions decrease in the order BPCl-1 > BPCl-2 > BPCl-0 which is roughly parallel to the C-Cl bond energy of these compounds and does not correlate with the chain length n, which corresponds to the distance required for the electron transfer.On the other hand, in the case of BPCl-3 and BPCl-4, the decay of the 410-nm band decreased about two orders of magnitude (5.5E5 and 1.2E6 s-1, respectively) and was characterized by a simultanous formation of a 330-nm band which is assigned to a spirocyclic radical.The G values of the corresponding 4-alkylbiphenyl formation were low for these compounds.On the basis of these observations, an intramolecular carbanionic displacement of the biphenyl radical anion on the chlorine center, which is a novel type of intramolecular SN2 reaction, has been concluded.Intramolecular reactions of bromo and iodo derivatives were also investigated and compared with those of corresponding chlorides.

Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia

Recently, irreversible inhibitors have attracted great interest in antitumors due to their advantages of forming covalent bonds to target proteins. Herein, some benzothiazepinone compounds (BTZs) have been designed and synthesized as novel covalent GSK-3β inhibitors with high selectivity for the kinase panel. The irreversible covalent binding mode was identified by kinetics and mass spectrometry, and the main labeled residue was confirmed to be the unique Cys14 that exists only in GSK-3β. The candidate 4-3 (IC50 = 6.6 μM) showed good proliferation inhibition and apoptosis-inducing ability to leukemia cell lines, low cytotoxicity on normal cell lines, and no hERG inhibition, which hinted the potential efficacy and safety. Furthermore, 4-3 exhibited decent pharmacokinetic properties in vivo and remarkably inhibited tumor growth in the acute promyelocytic leukemia (APL) mouse model. All the results suggest that these newly irreversible BTZ compounds might be useful in the treatment of cancer such as APL.

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.

Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles

An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.

Method for preparing alpha, beta-unsaturated carboxylic acid compound

The invention discloses a method for preparing an alpha, beta-unsaturated carboxylic acid compound, which comprises the following steps: 1) in an atmosphere containing carbon dioxide, heating and reacting a mixture containing hydrosilane and a copper catalyst to obtain a system I; and 2) adding a raw material containing alkyne and a nickel catalyst into the system I in the step 1), and heating to react. The method has the advantages of simple, easily available, cheap and stable raw materials, common, easily available and stable catalyst, mild reaction conditions, simple post-treatment, high yield and the like.

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo

The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.

Water-initiated hydrocarboxylation of terminal alkynes with CO2and hydrosilane

This work discloses a Cu(ii)-Ni(ii) catalyzed tandem hydrocarboxylation of alkynes with polysilylformate formed from CO2and polymethylhydrosiloxane that affords α,β-unsaturated carboxylic acids with up to 93% yield. Mechanistic studies indicate that polysilylformate functions as a source of CO and polysilanol. Besides, a catalytic amount of water is found to be critical to the reaction, which hydrolyzes polysilylformate to formic acid that induces the formation of Ni-H active species, thereby initiating the catalytic cycle.

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.

Electrical properties of amino acid substituted novel cinnamic acid compounds

Amino acid conjugates are combinations of one or more compounds, at least one of them active in terms of biological, pharmacological or physical. In this work, some novel amino acid conjugates, four different aldehydes (Pyrene, Naphthalene, Phenanthrene and Phenyl benzyl) have been chosen and from these initial materials four different amino acid conjugates were synthesized. The compounds from initial steps to final steps have been characterized by 1H and 13C APT NMR spectroscopy. The dielectric measurements were done by QuadTech 7600 LRC impedance analyzer. The dielectric constant (ε′) dielectric loss (ε’’) and ac conductivity (σ) values of amino acid conjugates in the frequency of 1 kHz and at 25 °C. The results show that the increase in conjugation affect the dielectric constant and conductivity.

Acrylamide benzoazepine derivatives as GSK-3beta inhibitors and applications thereof

The invention belongs to the technical field of medicinal chemistry, and discloses acrylamide benzoazepine derivatives serving as glycogen synthase kinase-3beta (GSK-3beta) inhibitors and applicationsof the acrylamide benzoaza derivatives. The derivatives are compounds shown as a formula (I) or pharmaceutically acceptable salts thereof. The compounds have good inhibitory activity on GSK-3beta andcan be used as selective inhibitors for preventing and treating GSK-3beta-related diseases, and the GSK-3beta-related diseases include cancer, neurodegenerative diseases and diabetes.