1631-29-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Chloro-phenyl)-pyrrole-2,5-dione is used as a reagent or intermediate for various chemical reactions in pharmaceutical manufacturing processes. Its specific effects and uses may vary depending on the context, but it plays a crucial role in the synthesis of certain pharmaceutical compounds.
Used in Chemical Manufacturing:
1-(4-Chloro-phenyl)-pyrrole-2,5-dione is also used as a reagent or intermediate in chemical manufacturing processes. Its presence in the synthesis of various chemical products highlights its importance in the chemical industry.
Note: The specific details about the properties, uses, or safety considerations of 1-(4-chloro-phenyl)-pyrrole-2,5-dione are not widely available, suggesting that more specialized knowledge or information may be necessary for its application in different industries.

InChI:InChI=1/C10H6ClNO2/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(12)14/h1-6H

Upstream product

• 108-31-6 maleic anhydride 
• 106-47-8 4-chloro-aniline 
• 108-95-2 phenol 
• 306935-74-0 3-[(4-chlorophenylamido)]propenoic acid 
• 72889-95-3 (Z)-3-(4-Chloro-phenylcarbamoyl)-acrylic acid methyl ester 
• 544476-12-2 C₁₂H₁₂ClNO₃ 
• 3052-50-4 monomethyl maleate 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 1751-80-0 4-chloro-N-(4-chlorobenzylidene)aniline 
• 7242-16-2 N-4-chlorophenyl-maleamic acid 
• 17722-52-0 N-[(4-chlorophenyl)]-4-oxo-4-[oxy]butane amide 
• 850148-32-2 3-chloro-1-(4-chlorophenyl)succinimide 
• 80310-34-5 C₃₅H₂₄Cl₂N₂O₄ 

Downstream Products

• 60437-32-3 2-(2-amino-4-methyl-7-oxo-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-6-yl)-N-(4-chloro-phenyl)-acetamide 
• 1005087-60-4 6-(4-chloro-phenyl)-8ξ-styryl-(4ar,7ac)-3,4a,7a,8-tetrahydro-pyrrolo[3',4':5,6]thiopyrano[2,3-d]thiazole-2,5,7-trione 
• 54819-75-9 2-(2-amino-4-oxo-4,5-dihydro-thiazol-5-yl)-N-(4-chloro-phenyl)-acetamide 
• 54819-67-9 2-(4-Methoxyphenyl)iminothiazolid-4-on-5-acet-(4-chloranilid) 
• 54819-66-8 2-(2-anilino-4-oxo-4,5-dihydro-thiazol-5-yl)-N-(4-chloro-phenyl)-acetamide 
• 63671-05-6 6-(4-chloro-phenyl)-8-(2-hydroxy-phenyl)-3,4a,7a,8-tetrahydro-pyrrolo[4',5':5,6]thiopyrano[2,3-d]thiazole-2,5,7-trione 
• 54819-69-1 2-[2-(4-chloro-anilino)-4-oxo-4,5-dihydro-thiazol-5-yl]-N-(4-chloro-phenyl)-acetamide 
• 63671-03-4 6-(4-chloro-phenyl)-8-furan-2-yl-3,4a,7a,8-tetrahydro-pyrrolo[3',4':5,6]thiopyrano[2,3-d]thiazole-2,5,7-trione 
• 134220-52-3 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-chloro-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-chloro-phenyl)-4a-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 134220-45-4 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-chloro-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-chloro-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 80310-45-8 C₄₁H₂₈Cl₂N₂O₅ 
• 80310-49-2 C₂₅H₁₄ClNO₂ 
• 80310-34-5 C₃₅H₂₄Cl₂N₂O₄ 

Relevant academic research and scientific papers

Identification of two arylimides as cholinesterase inhibitors and testing of propranolol addition on impaired rat memory

Alzheimer's disease (AD) is clearly linked to the decline of acetylcholine (ACh) effects in the brain. These effects are regulated by the hydrolytic action of acetylcholinesterase (AChE). Therefore, a central palliative treatment of AD is the administration of AChE inhibitors although additional mechanisms are currently described and tested for generating advantageous therapeutic strategies. In this work, we tested new arylamides and arylimides as potential inhibitors of AChE using in silico tools. Then, these compounds were tested in vitro, and two selected compounds, C7 and C8, as well as propranolol showed inhibition of AChE. In addition, they demonstrated an advantageous acute toxicity profile compared to that of galantamine as a reference AChE inhibitor. in vivo evaluation of memory performance enhancement was performed in an animal model of cognitive disturbance with each of these compounds and propranolol individually as well as each compound combined with propranolol. Memory improvement was observed in each case, but without a significant additive effect with the combinations.

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.

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.

Redox-Selective Iron Catalysis for α-Amino C-H Bond Functionalization via Aerobic Oxidation

Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)n 2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.

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.

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.).

Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones

A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).

Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles

The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.