19337-97-4

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-PYRIDYL)ACRYLIC ACID is used as a synthetic intermediate for the preparation of aminomethyl benzimidazoles, which act as inhibitors of gelatinase B. This application is significant in the development of potential therapeutic agents for various medical conditions.
Used in Antibacterial Applications:
In the pharmaceutical industry, 3-(3-PYRIDYL)ACRYLIC ACID is also used in the preparation of aminopyridines, which serve as antibacterial enoyl acyl carrier protein reductase inhibitors. These inhibitors play a crucial role in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Material Science:
3-(3-PYRIDYL)ACRYLIC ACID is used as an organic linker to connect d and f block metals, forming a 3D heterometallic coordination polymer with luminescence properties. This application is valuable in the field of material science, particularly in the development of new materials with unique optical and electronic properties.
Used in Chemical Synthesis:
In the chemical industry, 3-(3-PYRIDYL)ACRYLIC ACID is utilized in the synthesis of ethyl trans-3-(3-pyridyl)acrylate via esterification. This synthetic process expands the compound's applications in various chemical and industrial processes.

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

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

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.

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.

Synthesis and biological evaluation of 2,2-dimethylbenzopyran derivatives as potent neuroprotection agents

The development of novel neuroprotection agents is of great significance for the treatment of ischemic stroke. In this study, a series of compounds comprising 2,2-dimethylbenzopyran groups and cinnamic acid groups have been synthesized. Preferential combination principles and bioisostere that improved the neuroprotective effect of the compounds were identified for this series via biological activity assay in vitro. Meanwhile, a functional reversal group of the acrylamide amide resulted in the most active compounds. Among them, BN-07 significantly improved the morphology of neurons and obviously increased cell survival rate of primary neurons induced by oxygen glucose deprivation (OGD), superior to clinically used anti-ischemic stroke drug edaravone (Eda). Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents with more potency than Eda.

2,2-dimethylbenzopyran derivative and preparation method and use thereof

The invention belongs to the technical field of medicines, and discloses a 2,2-dimethylbenzopyran derivative and a preparation method and use of the 2,2-dimethylbenzopyran derivative. The derivative and pharmaceutically acceptable salt of the derivative have the structural formulae shown in the description, wherein Ar, Ar, X, Y and R1 are as described in the claims and the description. The preparation methods of the derivative and the pharmaceutically acceptable salt of the derivative comprise the following steps: the formula (I) is obtained by mainly taking acetaminophen as a raw material, and subjected to the reactions of Williamson ether formation, cyclization, hydrolysis, amide formation and the like; the formula II is obtained by mainly taking p-hydroxybenzaldehyde as a raw material, and subjected to the reactions of the Williamson ether formation, cyclization, Knoevenagel condensation, amide formation and the like. The derivative and the pharmaceutically acceptable salt ofthe derivative disclosed by the invention can be used for preparing neuroprotective agents and have better neuroprotective effects on ischemic stroke.

Semi-synthesis and Structure–Activity Relationship of Neuritogenic Oleanene Derivatives

(3S,4R)-23,28-Dihydroxyolean-12-en-3-yl (2E)-3-(3,4-dihydroxyphenyl)acrylate (1 a), which possesses significant neuritogenic activity, was isolated from the traditional Chinese medicine (TCM) plant, Desmodium sambuense. To confirm the structure and to assess biological activity, we semi-synthesized 1 a from commercially available oleanolic acid. A series of novel 1 a derivatives was then designed and synthesized for a structure–activity relationship (SAR) study. All synthetic derivatives were characterized by analysis of spectral data, and their neuritogenic activities were evaluated in assays with PC12 cells. The SAR results indicate that the number and position of the hydroxy groups on the phenyl ring and the triterpene moiety, as well as the length of the (saturated or unsaturated) alkyl chain that links the phenyl ring with the triterpene critically influence neuritogenic activity. Among all the tested compounds, 1 e [(3S,4R)-23,28-dihydroxyolean-12-en-3-yl (2E)-3-(3,4,5-trihydroxyphenyl)acrylate] was found to be the most potent, inducing significant neurite outgrowth at 1 μm.

Discovery of caffeic acid phenethyl ester derivatives as novel myeloid differentiation protein 2 inhibitors for treatment of acute lung injury

Myeloid differentiation protein 2 (MD2) is an essential molecule which recognizes lipopolysaccharide (LPS), leading to initiation of inflammation through the activation of Toll-like receptor 4 (TLR4) signaling. Caffeic acid phenethyl ester (CAPE) from propolis of honeybee hives could interfere interactions between LPS and the TLR4/MD2 complex, and thereby has promising anti-inflammatory properties. In this study, we designed and synthesized 48 CAPE derivatives and evaluated their anti-inflammatory activities in mouse primary peritoneal macrophages (MPMs) activated by LPS. The most active compound, 10s, was found to bind with MD2 with high affinity, which prevented formation of the LPS/MD2/TLR4 complex. The binding mode of 10s revealed that the major interactions with MD2 were established via two key hydrogen bonds and hydrophobic interactions. Furthermore, 10s showed remarkable protective effects against LPS-caused ALI (acute lung injury) in vivo. Taken together, this work provides new lead structures and candidates as MD2 inhibitors for the development of anti-inflammatory drugs.

Synthesis and evaluation of N-heteroaromatic ring-based analogs of piperlongumine as potent anticancer agents

Piperlongumine (PL) selectively targets a wide spectrum of cancer cells and induces their death by triggering various pathways, including apoptosis, necrosis and autophagy. However, the poor solubility is a serious concern for intensive study and clinical application. We synthesized its analogs 1–9 by replacement of the trimethoxyphenyl of PL with an N-heteroaromatic ring and/or not introduction of 2-Cl. These compounds improved aqueous solubility and displayed potent anticancer activity. The most active compound 9 selectively enhanced ROS levels in colon cancer cells and inhibited the cell proliferation but sparing non-tumor colon cells. Importantly, 9 significantly repressed tumor growth in an HCT-116 xenograft mouse model, suggesting that these N-heteroaromatic ring-based analogs of PL warrant further investigation.

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.

3-aryl acrylic acid and its derivatives viral anti-plant

The invention relates to an application of 3-aryl acrylic acid represented by a general formula (I) and a derivative thereof in pesticides, wherein the 3-aryl acrylic acid and the derivative thereof can be adopted as novel anti-plant virus agents, can be provided for well inhibiting tobacco mosaic virus, pepper virus, tomato virus, sweet potato virus, potato virus, melon virus, maize dwarf mosaic virus and the like, and can be provided for effectively preventing and controlling virus diseases of a plurality of crops such as tobacco, pepper, tomato, melon vegetables, grains, vegetables, beans and the like, especially tobacco mosaic diseases. (Wherein Ar and R are defined in an instruction).

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.