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Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(5-CHLORO-2-METHOXYPHENYL)ACRYLIC ACID is utilized as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique structure allows it to be a key component in developing new medications.
Used in Organic Synthesis:
In the realm of organic synthesis, (2E)-3-(5-CHLORO-2-METHOXYPHENYL)ACRYLIC ACID serves as a building block for the preparation of complex organic molecules. Its versatility in forming different chemical entities makes it valuable for creating a wide array of organic compounds.
Used in Medicinal Applications:
(2E)-3-(5-CHLORO-2-METHOXYPHENYL)ACRYLIC ACID may possess potential biological activities, and it is currently the subject of ongoing research. This research aims to explore its possible use in medicinal applications, which could lead to new therapeutic options in the future.

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Relevant academic research and scientific papers

Cinnamic acid derivatives linked to arylpiperazines as novel potent inhibitors of tyrosinase activity and melanin synthesis

A novel series of twenty-seven cinnamides constituted by cinnamic acid derivatives liked to 1-aryl piperazines were synthesized and evaluated for their potential inhibitory diphenolase activity of mushroom tyrosinase. Among them, the presence of a 3-chloro-4-fluorophenyl moiety at the N-1 position of piperazine ring was essential for a potent tyrosinase inhibitory effect, with the 3-nitrocinnamoyl (19p) and 2-chloro-3-methoxycinnamoyl (19t) derivatives as the most potent compounds of the series, with IC50 of 0.16 and 0.12 μM, respectively, resulting much active than kojic acid, whose IC50 value was 17.76 μM. In general, all compounds characterized by the presence of a 1-(3-chloro-4-fluorophenyl)piperazine moiety showed an excellent potency, and the nature, position and number of the substituents on the aryl of the cinnamic acid did not affect significantly the anti-tyrosinase activity. The molecular docking to the active site of the enzyme has been also performed to investigate the nature of enzyme-inhibitor interactions. Furthermore, for selected highly active compounds, their ability to inhibit melanogenesis in the A375 human melanoma cells and in vivo zebrafish model was also evaluated. One of the most potent compounds of series (19t) significantly reduced the pigmentation of zebrafish at 50 μM, unfortunately showing 100% mortality in the Fish Embryo Acute Toxicity (FET) test at the same concentration, Moreover, the zebrafish assay reveals that also compound 19r (IC50:0.51 μM against mushroom tyrosinase) effectively reduces melanogenesis with no acute toxicity effects and it could be proposed as potential candidate to treat tyrosinase-mediated hyperpigmentation.

2-Phenylcyclopropylmethylamine Derivatives as Dopamine D2Receptor Partial Agonists: Design, Synthesis, and Biological Evaluation

Partial agonist activity at the dopamine D2 receptor (D2R) is the primary pharmacological feature of the third-generation antipsychotics─aripiprazole, brexpiprazole, and cariprazine. However, all these drugs share a common phenyl-piperazine moiety as the primary pharmacophore. In this study, we designed and synthesized a series of novel compounds based on the 2-phenylcyclopropylmethylamine (PCPMA) scaffold and studied their pharmacological activity at the D2R. A number of potent D2R partial agonists were identified through binding affinity screening and functional activity profiling in both G protein and β-arrestin assays. The structure-functional activity relationship results showed that the spacer group is crucial for fine-tuning the intrinsic activity of these compounds. Compounds (+)-14j and (+)-14l showed good pharmacokinetic properties and an unexpected selectivity against the serotonin 2A (5-HT2A) receptor. Preliminary suppressive effects in a mouse hyperlocomotion model proved that these PCPMA-derived D2R partial agonists are effective as potential novel antipsychotics.

Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: A direct photocatalytic approach to cinnamic acids

The first workable application of β-nitrostyrenes and CBr4 as coupling partners for a highly stereoselective synthesis of (E)-cinnamic acids under visible light photoredox catalysis is reported. The reaction involves a radical denitrative tribromomethylation/hydrolysis cascade to afford (E)-cinnamic acids in excellent yields at room temperature in a one-pot procedure. Moreover, the implementation of visible light as a clean and inexpensive energy source and CBr4 as the latent source of carboxylic groups makes the protocol reconcilable with the present day scenario of organic synthesis.

Cinnamoylaminoalkyl-substituted benzenesulfonamide derivatives, processes for their preparation, their use, and pharmaceutical preparations comprising them

The present invention relates to cinnamoylaminoalkyl-substituted benzenesulfonamide derivatives of formula I in which A(1), A(2), A(3), R(1), R(2), R(3), R(4), X, Y, and Z have the meanings indicated in the claims. Compounds of formula I are valuable pharmaceutical active compounds which exhibit, for example, an inhibitory action on ATP-sensitive potassium channels in the cardiac muscle and/or in the cardiac nerve and are suitable, for example, for the treatment of disorders of the cardiovascular system such as coronary heart disease, arrhythmias, cardiac insufficiency or cardiomyopathies, or for the prevention of sudden cardiac death, or for improving decreased contractility of the heart. The invention furthermore relates to processes for the preparation of compounds of formula I, their use, and pharmaceutical preparations comprising them.