19077-60-2

Basic information

• Product Name: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE
• Synonyms: (1-p-ethoxyphenyl)-1h-pyrrole-5-dione;1-(4-ethoxyphenyl)maleimide;1-(p-ethoxyphenyl)-1h-pyrrole-2,5-dione;ephm;n-(p-ethoxyphenyl)-maleimid;N-(4-ETHOXYPHENYL)MALEIMIDE;ASISCHEM C66318;1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE
• CAS NO: 19077-60-2
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• Mol File: 19077-60-2.mol

Chemical Properties

• Boiling Point: 371.5 °C at 760 mmHg
• Flash Point: 178.5 °C
• Appearance: /
• Density: 1.272 g/cm³
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE(19077-60-2)
• EPA Substance Registry System: 1-(4-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE(19077-60-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 19077-60-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Ethoxyphenyl)-1H-pyrrole-2,5-dione is used as an active pharmaceutical ingredient for its potential as an anti-inflammatory and anti-cancer agent. Its biological activities make it a promising candidate for the development of new drugs to treat various diseases.
Used in Agrochemical Industry:
1-(4-Ethoxyphenyl)-1H-pyrrole-2,5-dione is used as an agrochemical compound for its ability to inhibit the growth of harmful microorganisms. This property makes it useful in the development of pesticides and other agricultural products to protect crops and enhance yield.
Used in Fluorescent Dye Applications:
1-(4-Ethoxyphenyl)-1H-pyrrole-2,5-dione is used as a fluorescent dye due to its unique optical properties. It has potential applications in various fields, such as bioimaging, diagnostics, and sensing.
Used in Organic Electronic Devices:
1-(4-Ethoxyphenyl)-1H-pyrrole-2,5-dione is used as a component in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, due to its electronic properties and potential for energy conversion and storage.

InChI:InChI=1/C12H11NO3/c1-2-16-10-5-3-9(4-6-10)13-11(14)7-8-12(13)15/h3-8H,2H2,1H3

Upstream product

• 108087-84-9 N-(4-ethoxy-phenyl)-maleamic acid 
• 51992-13-3 N-(4-ethoxy-phenyl)-malamic acid 
• 100122-11-0 1-(4-ethoxy-phenyl)-3-chloro-pyrrolidine-2,5-dione 
• 156-43-4 4-Ethoxyaniline 

Downstream Products

• 89143-28-2 1-(4-ethoxy-phenyl)-3-piperidin-1-yl-pyrrolidine-2,5-dione 
• 106058-53-1 1-(4-Ethoxy-phenyl)-3-(4-phenylsulfanyl-phenylamino)-pyrrolidine-2,5-dione 
• 106058-31-5 1-(4-Ethoxy-phenyl)-3-(4-methoxy-phenylamino)-pyrrolidine-2,5-dione 
• 106058-41-7 N-(4-ethoxy-phenyl)-aspartic acid-(4-ethoxy-phenylimide) 
• 485395-11-7 C₂₉H₂₃NO₆ 
• 485395-10-6 C₂₈H₂₁NO₆ 
• 374563-53-8 C₂₈H₂₀FNO₆ 

Relevant articles and documents

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo

A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

α-chlorosuccinimides - A new source for maleimides and succinimides

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Synthesis of N-Aryl/heteroaryl/-substituted-methyl-&α-(p-substituted anilino)succinimides as Antituberculosis Agents

A series of N-Aryl/heteroaryl/substituted-methyl-α-(p-substituted anilino)succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 0.39 μg/ml concentration.

Synthesis of N-Aryl/substituted-methyl/heteroaryl-&α-pyrrolidino/piperidino Succinimides as Antituberculosis Agents

A series of N-Aryl/substituted-methyl/heteroaryl-α-pyrrolidino- and piperidino-succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 1.56 μg/ml concentration.