1631-28-3

Usage

Uses

Used in Organic Synthesis:
1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of new compounds with potential applications in different industries.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE serves as a building block for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be incorporated into the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE is utilized as a building block for the synthesis of agrochemicals, such as pesticides and herbicides, to help improve crop protection and yield.
Used in Antioxidant and Radical Scavenging Applications:
Due to its antioxidant and radical scavenging properties, 1-(4-METHYLPHENYL)-1H-PYRROLE-2,5-DIONE is used in applications where it can help protect against oxidative stress and damage. This can be particularly useful in industrial processes where materials are exposed to conditions that may generate free radicals, as well as in medicinal applications where it can potentially protect cells from oxidative damage.

InChI:InChI=1/C11H9NO2/c1-8-2-4-9(5-3-8)12-10(13)6-7-11(12)14/h2-7H,1H3

Upstream product

• 108-31-6 maleic anhydride 
• 106-49-0 p-toluidine 
• 67-56-1 methanol 
• 24870-11-9 4-methylmaleanilic acid 
• 38046-98-9 3-chloro-1-(4-methylphenyl)pyrrolidine-2,5-dione 
• 3052-50-4 monomethyl maleate 
• 65344-80-1 methyl p-methylmaleanilate 
• 15485-32-2 N-(4-chlorobenzylidene)-4-toluidine 
• 2272-45-9 benzal-p-toluidine 
• 541-59-3 maleiimide 
• 557-24-4 maleamic acid 
• 55818-45-6 methyltriphenylphosphonium 4-methylbenzenesulfonate 
• 37904-03-3 3-p-tolylcarbamoyl-acrylic acid 

Downstream Products

• 3120-18-1 6,6-diphenyl-3-p-tolyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 3191-81-9 3-p-tolyl-spiro[3-aza-bicyclo[3.1.0]hexane-6,9'-fluorene]-2,4-dione 
• 60437-34-5 2-(2-amino-4-methyl-7-oxo-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-6-yl)-N-p-tolyl-acetamide 
• 41379-04-8 4,7-bis-benzo[1,3]dioxol-5-yl-1,3,9-trioxo-2-p-tolyl-2,3,3a,4,5,6,7,8,9,9b-decahydro-1H-benzo[e]isoindole-8-carboxylic acid ethyl ester 
• 57703-48-7 4,9-diphenyl-2-p-tolyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 57703-54-5 6,7-dimethyl-2,4,9-tri-p-tolyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 54819-65-7 2-Iminothiazolid-4-on-5-acet-(4-methylanilid) 
• 70464-66-3 5-p-tolyl-3-(2,4,6-trimethyl-phenyl)-(3ar,6ac)-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 54819-59-9 2-(4-Methoxyphenyl)-iminothiazolid-4-on-5-acet-(4-methylanilid) 
• 89143-26-0 3-piperidin-1-yl-1-p-tolyl-pyrrolidine-2,5-dione 
• 78817-63-7 5-Acetyl-4-phenyl-2-p-tolyl-3a,11c-dihydro-4H-6-oxa-2,11b-diaza-cyclopenta[c]phenanthrene-1,3,7-trione 
• 106369-04-4 (3aS,6aR)-2-Methyl-4,6-dioxo-5-p-tolyl-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid ethyl ester 
• 97406-83-2 1-(4-nitro-phenyl)-5-p-tolyl-3a,6a-dihydro-1H-pyrrolo[3,4-d][1,2,3]triazole-4,6-dione 
• 91199-17-6 exo-1,2,3,4-Tetrahydro-N-(4-methylphenyl)-1,4-imino-2,3-naphthalindicarboximid 

Relevant academic research and scientific papers

Diels-Alder reactions of five-membered heterocycles containing one heteroatom

Diels-Alder reactions of five-membered heterocycles containing one heteroatom with an N-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 °C gave bicyclic adduct 5. Cycloadditions of 3 with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound 5 cleanly rearranged, with loss of water, when treated with p-toluenesulfonic acid in toluene at 80 °C to give 4,7-dimethyl-2-p-tolylisoindoline-1,3-dione (6).

Room-Temperature Synthesis of Isoindolone Spirosuccinimides: Merger of Visible-Light Photocatalysis and Cobalt-Catalyzed C-H Activation

A room-temperature C-H bond functionalization of benzamides has been developed by merging a photocatalyst with a cobalt catalyst for the synthesis of isoindolone spirosuccinimides. The reaction proceeds in aerobic conditions and does not require any sacrificial external oxidants such as Ag(I) or Mn(III) salts. Visible light activates the photocatalyst, and it acts as an electron-transfer reagent and helps in the fundamental organometallic steps by modulating the oxidation state of the cobalt complex. This C-H bond functionalization and spirocyclization showed wide substrate scope and good functional group tolerance. A possible reaction mechanism was proposed from the experimental outcome, showing that C-H bond activation is irreversible and not the rate-determining step.

1,3-dipolar cycloaddition: Free catalytic synthesis and esophageal cancer activity of new 1,2,3-triazole-oxydianiline-maleimide hybrids

A new series of 1,2,3-triazole-oxydianiline-maleimide hybrids 12-15 was synthesized by using 1,3-dipolar cycloaddition reaction of N-Arylmaleimides 6-9 with 4,4'-oxybis(azidobenzene) 11 under an efficient and free catalytic reaction. All the newly synthesized hybrids were characterized by their 1H NMR, F-TIR, Mass spectral data and melting points. The cytotoxic activities (in vitro) of selected hybrids against esophageal cancer of human cell line (SKG) were evaluated by MTT assay. Among them, hybrid 13 exhibited a potent inhibition activity with the IC50 value of 1.61±0.01 μM against esophageal cancer cell (SKG). Cellular mechanism investigations in esophageal carcinoma cells (SKG) elucidated that hybrid 13 inhibited cell growths in vitro and arrested cell cycle at an environmental phase. These results revealed that hybrid 13 holds a promising anticancer agent with the enhancement of further clinical applications in drug discovery field.

Application of maleimide compound as chitin synthase inhibitor

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.

Regioselective hydroarylation and arylation of maleimides with indazoles: Via a Rh(iii)-catalyzed C-H activation

Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma

Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.

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 of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).

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.

Nickel(II) Tetraphenylporphyrin as an Efficient Photocatalyst Featuring Visible Light Promoted Dual Redox Activities

Nickel(II) tetraphenylporphyrin (NiTPP) is presented as a robust, cost-effective and efficient visible light induced photoredox catalyst. The ground state electrochemical data (CV) and electronic absorption (UV-Vis) spectra reveal the excited state redox potentials for [NiTPP]*/[NiTPP].? and NiTPP].+/[NiTPP]* couples as +1.17 V and ?1.57 V vs SCE respectively. The potential values represent NiTPP as a more potent photocatalyst compare to the well-explored [Ru(bpy)3]2+. The non-precious photocatalyst exhibits excited state redox reactions in dual fashions, i. e., it is capable of undergoing both oxidative as well as reductive quenching pathways. Such versatility of a photocatalyst based on first-row transition metals is very scarce. This unique phenomenon allows one to perform diverse types of redox reactions by employing a single catalyst. Two different sets of chemical reactions have been performed to represent the synthetic utility. The catalyst showed superior efficiency in both carbon-carbon and carbon-heteroatom bond-forming reactions. Thus, we believe that NiTPP is a valuable addition to the photocatalyst library and this study will lead to more practical synthetic applications of earth-abundant-metal-based photoredox catalysts. (Figure presented.).