24870-11-9

Basic information

• Product Name: 4-OXO-4-(4-TOLUIDINO)BUT-2-ENOIC ACID
• Synonyms: ASISCHEM Z45642;4-OXO-4-(4-TOLUIDINO)BUT-2-ENOIC ACID;N-(4-METHYLPHENYL)MALEAMIC ACID;(Z)-4-(4-Methylanilino)-4-oxo-2-butenoic acid;(Z)-4-(4-Methylphenylamino)-4-oxo-2-butenoic acid;N-(4-Methylphenyl)maleamidic acid;N-(p-Tolyl)maleamidic acid;N-p-Tolylmaleamidic acid
• CAS NO: 24870-11-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 24870-11-9.mol
• Article Data: 33

Chemical Properties

• Melting Point: 193 °C(Solv: ethanol (64-17-5))
• Boiling Point: 446.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.282±0.06 g/cm3(Predicted)
• PKA: 2.81±0.25(Predicted)
• CAS DataBase Reference: 4-OXO-4-(4-TOLUIDINO)BUT-2-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-OXO-4-(4-TOLUIDINO)BUT-2-ENOIC ACID(24870-11-9)
• EPA Substance Registry System: 4-OXO-4-(4-TOLUIDINO)BUT-2-ENOIC ACID(24870-11-9)

Safety Data

• Hazardous Substances Data: 24870-11-9(Hazardous Substances Data)

Upstream product

• 108-31-6 maleic anhydride 
• 106-49-0 p-toluidine 

Downstream Products

• 1221263-63-3 3-(p-tolylcarbamoyl)-3-(benzylthio)propanoic acid 
• 1631-28-3 N-p-tolylphenylmaleimide 
• 38046-98-9 3-chloro-1-(4-methylphenyl)pyrrolidine-2,5-dione 
• 19990-25-1 5-p-tolylimino-5H-furan-2-one 
• 106691-37-6 2-(3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-N-p-tolyl-acetamide 
• 65344-76-5 2-Decylsulfanyl-N-p-tolyl-succinamic acid 
• 64120-71-4 2-decylsulfanyl-N-phenyl-succinamic acid 
• 65344-80-1 methyl p-methylmaleanilate 

Relevant articles and documents

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.

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.

Triethylamine-catalyzed synthesis of oxazepine from maleamic acids

2-Thioxo-1,3-oxazepine-4,7-dione compounds were obtained via triethylamine-catalyzed condensation of maleamic acids with thiophosgene under anhydrous conditions. This method features relatively a simple methodology, use of inexpensive reagents, convenient operating conditions and high yields.