38489-74-6

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(2,5-Dimethoxyphenyl)-2-propenoic acid is used as a pharmaceutical compound for its potential therapeutic applications. Its unique structure, including the cinnamic moiety and methoxy groups, may contribute to its interaction with biological targets, making it a candidate for drug development.
Used in Chemical Research:
(2E)-3-(2,5-Dimethoxyphenyl)-2-propenoic acid is used as a research compound in the field of organic chemistry. Its structural features and reactivity can be studied to understand the properties of phenylpropanoids and cinnamic acids, which may lead to the discovery of new chemical reactions or applications.
Used in Material Science:
(2E)-3-(2,5-Dimethoxyphenyl)-2-propenoic acid is used as a component in the development of new materials. Its chemical structure may allow it to be incorporated into polymers or other materials, potentially improving their properties or providing new functionalities.

Upstream product

• 141-82-2 malonic acid 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 110-89-4 piperidine 
• 117646-10-3 5-(2',5'-dimethoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 10538-49-5 3-(2,5-dimethoxyphenyl)propanoic acid 
• 103796-19-6 2,5-dimethoxy-trans-cinnamic acid amide 
• 116406-20-3 Methyl (E)-3-(2,5-Dimethoxyphenyl)propenoate 
• 15804-86-1 (2E)-ethyl 3-(2,5-dimethoxyphenyl)propenoate 
• 52428-09-8 4,7-dimethoxyindan-1-one 
• 162019-02-5 4,7-dimethoxy-6-(2,4,5-trichloro-3,6-dimethoxybenzyl)indanone 
• 162019-04-7 6'-bromo-4,7-dimethoxy-6-(2,4,5-trichloro-3,6-dimethoxybenzyl)-2,2'-spirobiindane 
• 162018-97-5 6'-formyl-4,7-dimethoxy-6-(2,4,5-trichloro-3,6-dimethoxybenzyl)-2,2'-spirobiindane 
• 162019-03-6 6'-bromo-4,7-dimethoxy-6-(2,4,5-trichloro-3,6-dimethoxybenzyl)-2,2'-spirobiindan-1-one 
• 3600-86-0 2,5-dimethoxyphenethylamine 
• 72205-78-8 3-(2,5-dimethoxy-phenyl)-propionic acid amide 
• 21581-41-9 2,5-dihydroxyphenylethylamine 
• 3489-95-0 (2,5-dimethoxy-phenethyl)-methyl-amine 
• 72018-06-5 ethyl E-3-(2,5-dimethoxyphenyl)propanoate 

Relevant academic research and scientific papers

Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol

An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.

Sesquiterpene lactone-cinnamic acid derivative and salt, pharmaceutical composition and application thereof

The invention provides application of sesquiterpene lactone-cinnamic acid derivatives shown as a formula (I) and salts thereof in preparation of medicines for treating cancers and auxiliary medicinesfor treating cancers.

Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents

Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with “oxadiazole”. A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound 32 displayed potent anti-tubercular activity (IC50 = 0.045 μg/mL). Molecular docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the experimental findings providing a platform for structure based hit-to-lead development.

Synthesis and structure-activity relationship studies of parthenolide derivatives as potential anti-triple negative breast cancer agents

Triple-negative breast cancer (TNBC) is the most aggressive cancers with a high recurrence rate and rapidly acquired drug resistance among various breast cancer subtypes. There is no specific drug for treatment of TNBC. Discovery of therapeutic agents with unique modes of actions is urgently needed. In this study, a series of seventy parthenolide derivatives was designed, synthesized, and evaluated for their anti-TNBC activities. Compound 7d exhibited the most potent activity against different breast cancer cells with IC50 values ranging from 0.20 μM to 0.27 μM, which demonstrated 11.6- to 18.6-fold improvement comparing to that of the parent compound parthenolide with IC50 values of 2.68–4.63 μM. It is worth to note that 7d was more active than the positive control drug ADR. Moreover, compound 7d could induce apoptosis of SUM-159 cells through mitochondria pathway and cause G1 phase arrest of SUM-159 cells. These findings indicate that compound 7d deserves further studies as a lead compound for ultimate discovery of effective anti-TNBC drug.

Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase

Novel imatinib amide derivatives (a1-28, b1-9) were synthesized and evaluated for their biological activities. All compounds were characterized by 1H NMR, MS and elemental analysis. Among all the derivatives, compounds a4, a10, a21, b1 and b2 displayed the most significant ability of inhibiting K562 cell proliferation with the IC50 values of 0.67, 0.66, 0.65, 0.59 and 0.62 μM, respectively, indicating that these compounds were potent inhibitors of Bcr-Abl in leukemic K562 cells, comparable to the reference compound imatinib. Molecular docking study was performed to position compounds a21 and b1 into the active site of Abl to determine the probable binding modes

Synthesis and leishmanicidal activity of cinnamic acid esters: Structure-activity relationship

Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15-17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12-17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18-20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies.

A practical and convenient protocol for the synthesis of (E)-α,β-unsaturated acids

α,β-Unsaturated acids are very useful and versatile reagents in organic synthesis. A novel, practical, and convenient catalytic protocol comprising FeCl3·6H2O (0.5 mol %) and H 2O (1 equiv) in CH3NO2 is described for the rapid synthesis of α,β-unsaturated acids with high E-stereoselectivity under both microwave and conventional heating conditions with high TON and TOF values. This powerful approach efficiently demonstrated the utility of biomass derived aldehydes to build chemical agents used as fuel additives. The method proved to be scalable to gram scale synthesis.

Synthesis of trans-cinnamic acids from aryl aldehydes and aryl aldehyde bisulfite adducts with malonic acid using piperazine

Piperazine as a new reagent for the condensation of aryl aldehydes and their bisulfite adducts with malonic acid are described which afford the corresponding cinnamic acids in excellent yields and short reaction times in the absence of solvents under microwave irradiation.

Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium

The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.

A one-pot synthesis of 3-amino-3-arylpropionic acids

3-Aminopropionic acids (β-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these β-amino acids. The reaction mechanism of this one-pot synthesis of β-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed.