15254-22-5

Basic information

• Product Name: trans-3-(2,5-dimethylbenzoyl)acrylic acid
• Synonyms: trans-3-(2,5-dimethylbenzoyl)acrylic acid
• CAS NO: 15254-22-5
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.22
• Mol File: 15254-22-5.mol

Chemical Properties

• Melting Point: 89-90 °C
• Boiling Point: 385.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.168±0.06 g/cm3(Predicted)
• PKA: 3.19±0.10(Predicted)
• CAS DataBase Reference: trans-3-(2,5-dimethylbenzoyl)acrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-(2,5-dimethylbenzoyl)acrylic acid(15254-22-5)
• EPA Substance Registry System: trans-3-(2,5-dimethylbenzoyl)acrylic acid(15254-22-5)

Safety Data

• Hazardous Substances Data: 15254-22-5(Hazardous Substances Data)

Upstream product

• 108-31-6 maleic anhydride 
• 106-42-3 para-xylene 

Downstream Products

• 105493-04-7 C₁₂H₁₁ClO₂ 
• 15308-14-2 (+/-)-3.4-dimethyl-6t-(2,5-dimethyl-benzoyl)-cyclohexene-⁽³⁾-carboxylic acid-(1r) 
• 81353-15-3 C₁₂H₁₁ClO₂ 
• 81353-16-4 (E)-4-(2,5-dimethylphenyl)-4-oxo-N-phenyl-2-butenamide 

Relevant articles and documents

Preparation method of benzoyl-containing acrylic acid podophyllotoxin ester derivative and application of benzoyl-containing acrylic acid podophyllotoxin ester derivative in tumor suppression

The invention discloses a benzenesulfonamide phenylacetic acid podophyllotoxin carboxylic ester derivative as well as a synthesis method and application thereof, belongs to the technical field of chemical pharmacy, and particularly relates to a podophyllotoxin derivative and application thereof in tumor inhibition. Corresponding benzenesulfonamide phenylacetic acid is connected with podophyllotoxin through a synthesis means to obtain corresponding ester derivatives, and in-vitro anti-tumor activity research shows that the podophyllotoxin carboxylic ester derivatives have very strong inhibitory activity on tumor cell strains.

Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR

In this study, a series of shikonin derivatives combined with benzoylacrylic had been designed and synthesized, which showed an inhibitory effect on both tubulin and the epidermal growth factor receptor (EGFR). In vitro EGFR and cell growth inhibition assay demonstrated that compound PMMB-317 exhibited the most potent anti-EGFR (IC50 = 22.7 nM) and anti-proliferation activity (IC50 = 4.37 μM) against A549 cell line, which was comparable to that of Afatinib (EGFR, IC50 = 15.4 nM; A549, IC50 = 6.32 μM). Our results on mechanism research suggested that, PMMB-317 could induce the apoptosis of A549 cells in a dose- and time-dependent manner, along with decrease in mitochondrial membrane potential (MMP), production of ROS and alterations in apoptosis-related protein levels. Also, PMMB-317 could arrest cell cycle at G2/M phase to induce cell apoptosis, and inhibit the EGFR activity through blocking the signal transduction downstream of the mitogen-activated protein MAPK pathway and the anti-apoptotic kinase AKT pathway; typically, such results were comparable to those of afatinib. In addition, PMMB-317 could suppress A549 cell migration through the Wnt/β-catenin signaling pathway in a dose-dependent manner. Additionally, molecular docking simulation revealed that, PMMB-317 could simultaneously combine with EGFR protein (5HG8) and tubulin (1SA0) through various forces. Moreover, 3D-QSAR study was also carried out, which could optimize our compound through the structure-activity relationship analysis. Furthermore, the in vitro and in vivo results had collectively confirmed that PMMB-317 might serve as a promising lead compound to further develop the potential therapeutic anticancer agents.

Synthesis and biological activity evaluation of shikonin benzoylacrylic carboxylic ester derivatives

The invention belongs to the technical field of chemical pharmacy and specifically relates to shikonin derivatives and application thereof to tumor inhibition aspect. A synthesizing method is utilizedfor connecting corresponding benzoylacrylic derivative

Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields

Antiproliferative activity of 27 phenyl-substituted 4-aryl-4-oxo-2-butenoic acids (aroylacrylic acids) toward Human cervix carcinoma (HeLa), Human chronic myelogenous leukemia (K562) and Human colon tumor (LS174) cell lines in vitro are reported. Compounds are active toward all examined cell lines. The most active compounds bear two or three branched alkyl or cycloalkyl substituents on phenyl moiety having potencies in low micromolar ranges. One of most potent derivatives arrests the cell cycle at S phase in HeLa cells. The 3D QSAR study, using molecular interaction fields (MIF) and derived alignment independent descriptors (GRIND-2), rationalize the structural characteristics correlated with potency of compounds. Covalent chemistry, most possibly involved in the mode of action of reported compounds, was quantitatively accounted using frontier molecular orbitals. Pharmacophoric pattern of most potent compounds are used as a template for virtual screening, to find similar ones in database of compounds screened against DTP-NCI 60 tumor cell lines. Potency of obtained hits is well predicted.

4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields

Synthesis and anticholinesterase activity of 4-aryl-4-oxo-N-phenyl-2-aminylbutyramides, novel class of reversible, moderately potent cholinesterase inhibitors, are reported. Simple substituent variation on aroyl moiety changes anti-AChE activity for two orders of magnitude; also substitution and type of hetero(ali)cycle in position 2 of butanoic moiety govern AChE/BChE selectivity. The most potent compounds showed mixed-type inhibition, indicating their binding to free enzyme and enzyme-substrate complex. Alignment-independent 3D QSAR study on reported compounds, and compounds having similar potencies obtained from the literature, confirmed that alkyl substitution on aroyl moiety of molecules is requisite for inhibition activity. The presence of hydrophobic moiety at close distance from hydrogen bond acceptor has favorable influence on inhibition potency. Docking studies show that compounds probably bind in the middle of the AChE active site gorge, but are buried deeper inside BChE active site gorge, as a consequence of larger BChE gorge void.

2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids selectively suppressed proliferation of neoplastic human HeLa cells. A SAR/QSAR study

A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 μM/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations ( 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.