4733-76-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-4-(butylamino)-4-oxobut-2-enoic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex molecular structures, contributing to the development of new drugs with improved therapeutic properties.
Used in Organic Chemistry:
As a building block in organic chemistry, (2E)-4-(butylamino)-4-oxobut-2-enoic acid is utilized in the creation of diverse organic compounds, facilitating the advancement of chemical research and the discovery of novel chemical entities.
Used in Antioxidant Applications:
(2E)-4-(butylamino)-4-oxobut-2-enoic acid is studied for its potential antioxidant properties, which may be harnessed to develop treatments that protect cells from oxidative damage and related diseases.
Used in Anti-inflammatory Applications:
(2E)-4-(butylamino)-4-oxobut-2-enoic acid is also being investigated for its anti-inflammatory properties, suggesting its potential use in the development of medications aimed at reducing inflammation and associated symptoms in various conditions.

Upstream product

• 108-31-6 maleic anhydride 
• 109-73-9 N-butylamine 

Downstream Products

• 80991-63-5 N-n-butylmaleisoimidium perchlorate 
• 92989-16-7 (Z)-Butyl methyl maleamate 
• 189129-27-9 (E)-Butyl methyl maleamate 
• 108-31-6 maleic anhydride 
• 109-73-9 N-butylamine 
• 27396-39-0 maleic acid N-butylisoimide 
• 115355-58-3 1-Butyl-3-[1-dimethylamino-meth-(Z)-ylidene]-4-[(E)-phenylimino]-pyrrolidine-2,5-dione 
• 85038-14-8 1-butyl-3-(phenylamino)-1H-pyrrole-2,5-dione 
• 41187-40-0 1-butyl-3-(phenylamino)pyrrolidine-2,5-dione 

Relevant academic research and scientific papers

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.

Comparison of pH-sensitive degradability of maleic acid amide derivatives

We synthesized five maleic acid amide derivatives (maleic, citraconic, cis-aconitic, 2-(2′-carboxyethyl) maleic, 1-methyl-2-(2′- carboxyethyl) maleic acid amide), and compared their degradability for the future development of pH-sensitive biomaterials with tailored kinetics of the release of drugs, the change of charge density, and the degradation of scaffolds. The degradation kinetics was highly dependent upon the substituents on the cis-double bond. Among the maleic acid amide derivatives, 2-(2′-carboxyethyl) maleic acid amide with one carboxyethyl and one hydrogen substituent showed appropriate degradability at weakly acidic pH, and the additional carboxyl group can be used as a pH-sensitive linker.

A facile and economical procedure for the synthesis of maleimide derivatives using an acidic ionic liquid as a catalyst

Seven maleimide derivatives were synthesized in good yields and high purity from the corresponding maleamic acids using a Bronsted acidic room temperature ionic liquid (RTIL) as a catalyst. The products were obtained through merely a decanting and removal of the solvent, suggesting that this procedure is superior to the conventional routes, in which the strong organic/inorganic acids were used as the catalysts, as well as a complicated post-processing procedure for the separation and purification of the products was employed.

Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide

A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.

First triphenylphosphine promoted reduction of maleimides to succinimides

Triphenylphosphine (TPP) in refluxing methanol effectively reduces maleimides 1a-g to the corresponding succinimides 2a-g in good yields. It was observed that some maleimides obtained from aromatic halogen compounds 1h-j were transformed into the corresponding succinamic acid methyl esters 3a-c by this reaction.

Synthesis and antimicrobial activities of N-substituted imides

In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.

Synthesis of 2'-deoxyuridine and 5-fluoro-2'-deoxyuridine derivatives and evaluation in antibody targeting studies

Derivatives of 2'-deoxyuridine and of the anticancer agent 5-fluoro-2'- deoxyuridine (FdUR) were linked indirectly via a human serum albumin carrier (HSA) to the murine antiosteosarcoma monoclonal antibody 791T/36. Starting from the 2'-deoxyuridines 1a an

Antitumor chemotherapy. XIV. Cytotoxic activity of compounds possessing an ethylenic double bond substituted at the α and β positions with an electron attracting group

The authors have previously shown that molecules possessing an ethylene double bond, activated by one or 2 electron attracting substituents, show a cytotoxic activity which must be connected with the addition of a cellular nucleophil to their double bond. This correlation has been extended to N alkylmaleinimides and different compounds with paraquinonine structure. The compounds examined possess a distinct cytotoxic antitumor activity which is, however, inferior to that of α nitro stilbenes and β nitro styrenes, the simplified analogs of aristolochic acid.