1126-74-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Pyridineacrylic acid is used as an inhibitor for peptidylglycine amidating monooxygenase (PAM), an enzyme involved in the post-translational modification of peptides. By inhibiting PAM, 3-Pyridineacrylic acid can potentially be utilized in the development of therapeutic agents for various diseases and conditions related to the misregulation of peptide amidation.
Used in Chemical Synthesis:
3-Pyridineacrylic acid, due to its unique chemical structure, can be used as a building block or intermediate in the synthesis of various complex organic compounds. Its reactivity and functional groups make it a versatile compound for use in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
As a compound with specific inhibitory properties, 3-Pyridineacrylic acid can be employed in research and development for studying the role of PAM in biological processes and the potential therapeutic applications of targeting this enzyme. It can also be used as a tool to investigate the structure-activity relationship of PAM inhibitors and to develop more potent and selective compounds for various applications.

InChI:InChI=1/C8H7NO2/c10-8(11)4-3-7-2-1-5-9-6-7/h1-6H,(H,10,11)/p-1/b4-3+

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 141-82-2 malonic acid 
• 108-24-7 acetic anhydride 
• 6443-86-3 3-(3-pyridinyl)-2-propenenitrile 
• 59607-99-7 ethyl (E)-3-(pyridin-3-yl)acrylate 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 54356-28-4 (Z)-3-(3-pyridyl)acrylonitrile 
• 54356-27-3 (E)-3-(pyridin-3-yl)acrylonitrile 
• 872-85-5 pyridine-4-carbaldehyde 
• 626-55-1 3-Bromopyridine 
• 100390-47-4 (E)-3-(3-pyridinyl)acrylic acid butyl ester 
• 100390-47-4 C₁₂H₁₅NO₂ 

Downstream Products

• 1822-31-7 3-(piperidin-3-yl)propionic acid 
• 3724-19-4 3-pyridine propionic acid 
• 62247-21-6 3-amino-3-(pyridin-3-yl)propanoic acid 
• 1126-73-4 (E)-3-(pyridin-3-yl)acrylamide 
• 59607-99-7 ethyl (E)-3-(pyridin-3-yl)acrylate 
• 118420-64-7 (E)-N-[4-(4-Benzhydrylidene-piperidin-1-yl)-butyl]-3-pyridin-3-yl-acrylamide 
• 118420-63-6 (E)-N-{4-[4-(Hydroxy-diphenyl-methyl)-piperidin-1-yl]-butyl}-3-pyridin-3-yl-acrylamide 
• 118420-27-2 (E)-N-{4-[4-(Phenyl-m-tolyl-methyl)-piperazin-1-yl]-butyl}-3-pyridin-3-yl-acrylamide 
• 118420-29-4 (E)-N-(4-{4-[(3,4-Dimethyl-phenyl)-phenyl-methyl]-piperazin-1-yl}-butyl)-3-pyridin-3-yl-acrylamide 
• 118420-28-3 (E)-N-{4-[4-(Phenyl-p-tolyl-methyl)-piperazin-1-yl]-butyl}-3-pyridin-3-yl-acrylamide 
• 118437-09-5 (E)-N-[4-(4-Di-p-tolylmethyl-piperazin-1-yl)-butyl]-3-pyridin-3-yl-acrylamide 
• 118420-24-9 (E)-N-(4-{4-[(4-Fluoro-phenyl)-phenyl-methyl]-piperazin-1-yl}-butyl)-3-pyridin-3-yl-acrylamide 
• 118420-25-0 (E)-N-(4-{4-[(4-Chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-butyl)-3-pyridin-3-yl-acrylamide 
• 118420-26-1 (E)-N-(4-{4-[(4-Methoxy-phenyl)-phenyl-methyl]-piperazin-1-yl}-butyl)-3-pyridin-3-yl-acrylamide 

Relevant academic research and scientific papers

Environmentally benign and energy efficient methodology for condensation: An interesting facet to the classical Perkin reaction

We have reported use of biodegradable deep eutectic solvent (DES) based on choline chloride and urea, for the synthesis of cinnamic acid and its derivatives via Perkin reaction. The reaction proceeds efficiently under mild condition without use of additional catalyst with better yields. Ease of recovery and reusability of solvent with consistent activity makes this method efficient and environmentally benign. This method is also energy efficient and easy to handle.

Coordination polymers of organic polymers synthesized via photopolymerization of single crystals: Two-dimensional hydrogen bonding layers with amazing shock absorbing nature

Crystalline coordination polymers of organic polymers (CPOPs) were synthesized via photopolymerization of Ag(i) coordination polymers of dienes which have a self-templating nature due to the formation of N-H...O hydrogen bonded layers. The shock absorbing nature of the H-bonded layer facilitated the SCSC [2+2] transformation upon irradiation to produce CPOPs. This journal is the Partner Organisations 2014.

Synthesis of cinnamic acid derivatives in a water-insoluble ionic liquid

A number of cinnamic acid derivatives have been synthesised from commercially available aromatic aldehydes and propanedioic acid in a water-insoluble ionic liquid (1-butyl-3-methylimidazolium hexafluorophosphate, [bmim]PF6) in high yields in the presence of small catalytic amounts of piperidine. The ionic liquid can be reused at least five times.

Isoreticular Expansion of Metal–Organic Frameworks via Pillaring of Metal Templated Tunable Building Layers: Hydrogen Storage and Selective CO2 Capture

The deliberate construction of isoreticular eea-metal–organic frameworks (MOFs) (Cu-eea-1, Cu-eea-2 and Cu-eea-3) and rtl-MOFs (Co-rtl-1 and Co-rtl-2) has been accomplished based on the ligand-to-axial pillaring of supermolecular building layers. The use of different metal ions resulted in two types of supermolecular building layers (SBLs): Kagome (kgm) and square lattices (sql) which further interconnect to form anticipated 3D-MOFs. The isoreticular expansion of (3,6)-connected Cu-MOFs has been achieved with desired eea-topology based on kgm building layers. In addition, two (3,6)-connected Co-rtl-MOFs were also successfully constructed based on sql building layers. The Cu-eea-MOFs were shown to act as hydrogen storage materials with appreciable amount of hydrogen uptake abilities. Moreover Cu-eea-MOFs have also exhibited remarkable CO2 capture ability at ambient condition compared to nitrogen and methane, due to the presence of amide functionalities.

Structural features of pyridylcinnamic acid dimers and their extended hydrogen-bonded aggregations

The conformational as well as the structure-forming properties of E-3-(x-pyridyl)propenoic acids (x = 2, 3 or 4) have been studied with a combination of computational and spectroscopic methods. IR spectroscopy revealed that in the solid state the zwitterionic species predominate, while NMR measurements showed that dimers, kept together by strong CO?HO hydrogen bonds, were formed in a dipolar aprotic solvent (DMSO). In concentrated solution, extended aggregation occurred through the cooperative effect of (aromatic) C-H?N weak hydrogen bonds. Conformational search was performed at the HF/6-31G(d,p) level of theory. Comparison with experimental values as well as benchmarking calculations at several different levels of theory to probe the performance of the methods, B3LYP/6-31G++(d,p) method was found to be able to provide reasonable geometries as well as quantitative formation energies for the dimers and the tetramers, too.

Strategic Approach to 8-Azacoumarins

8-Azacoumarins have emerged as a promising class of compounds but are rarely explored due to challenging access. A novel, general, and practical method is provided for this class of compounds. The key lactonization step employs trans-acrylic acid attached pyridine N-oxides as the starting material, with acetic anhydride as both the activation agent and the solvent. Multiple transformations were involved in this reaction, including conjugate addition, nucleophilic aromatic substitution, and elimination. These studies provide the basis for access to 8-azacoumarins, enabling future work including the discovery and development of novel coumarin-type drugs, fluorescent probes, photolabile protecting groups, and other active molecules.

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.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

Photocatalytic decarboxylative alkenylation of α-amino and α-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.

Orthoquinone compound, as well as preparation method and medicinal application thereof

The invention discloses an active small molecular compound simultaneously targeted to NQO1 and NAMPT, as well as a preparation method and a medicinal application thereof, and particularly relates to an orthoquinone compound or a pharmaceutically acceptable salt, solvate, predrug, ester, raceme and isomer thereof, and a medicine composition comprising the compounds, and applications of these compounds and medicine compositions in preparation of anti-tumor drugs. In the invention, by reasonably jointing an activating substrate tanshinone IIA of the NQO1 and the pharmacophores on the NAMPT inhibitor, the NQO1 substrate/NAMPT inhibitor is obtained, so that the compounds can be reductively activated by the NQO1 and meanwhile can inhibit the activity of the NAMPT, thus consuming the NAD+ and inhibiting biosynthesis of the NAD+ and showing a better tumor inhibiting activity. The orthoquinone compounds or medicine compositions thereof that simultaneously target to the NQO1 and the NAMPT have extensive application prospect and are hopeful to be anti-tumor drugs.