1082-85-5

Usage

Uses

Used in Chemical Synthesis:
N-(4-Acetylphenyl)maleimide is used as a cross-linking agent for the reversible conjugation of thiol-containing compounds. This application is particularly useful in the field of chemical synthesis, where it can help create stable and functional molecules with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(4-Acetylphenyl)maleimide is utilized as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to form reversible conjugations with thiol-containing compounds allows for the development of novel therapeutic agents with improved pharmacological properties.
Used in Biochemical Research:
N-(4-Acetylphenyl)maleimide is also employed in biochemical research as a tool to study the interactions between proteins and other biomolecules. By forming reversible conjugations with thiol groups, it can help researchers understand the structure and function of proteins, as well as their role in various biological processes.
Used in Material Science:
In the field of material science, N-(4-Acetylphenyl)maleimide can be used to develop new materials with specific properties. Its ability to form reversible conjugations with thiol-containing compounds can be exploited to create materials with enhanced stability, reactivity, or other desired characteristics.

InChI:InChI=1/C12H9NO3/c1-8(14)9-2-4-10(5-3-9)13-11(15)6-7-12(13)16/h2-7H,1H3

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 75-36-5 acetyl chloride 
• 108-31-6 maleic anhydride 
• 99-92-3 p-aminobenzophenone 
• 24870-12-0 (Z)-4-(4-acetylphenylamino)-4-oxobut-2-enoic acid 
• 24870-12-0 N-(4-acetyl-phenyl)-maleamic acid 

Downstream Products

• 28202-80-4 1-(4-acetyl-phenyl)-3-((E)-6-amino-benzo[1,3]dioxol-5-ylmethylene)-pyrrolidine-2,5-dione 
• 28081-70-1 N-(4-acetyl-phenyl)-2-(6-oxo-5,6-dihydro-[1,3]dioxolo[4,5-g]quinolin-7-yl)-acetamide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of anti-tubercular activity of Schiff bases of 2-Amino thiazoles

Tuberculosis, an infectious disease, has been reported to cause the death of 1.5 million in 2018. Due to the emergence of Multi-Drug Resistant-TB, Extensively Drug Resistant-TB, and Totally Drug Resistant-TB, many first-line and second-line drugs have been found in-effective. New drugs introduced in TB regimens such as pretomanid, bedaquiline and linezolid have been associated with toxicities. Hence, there is an urgent need for introducing safe and cost-effective antitubercular drugs. In this study, a series of Schiff bases of 2-amino thiazoles were synthesized and evaluated for their anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain by Microplate Alamar Blue assay (MABA) method. N-[4-(2-Amino-thiazol-4-yl)-phenyl]-benzamide derivative with 2-nitro (5c2), 4-hydroxy (5c4) substitution, 2-[4-(2-Amino-thiazol-4-yl)-phenyl]-isoindole-1,3-dione derivatives with 3,4,5-trimethoxy substitution (5b1) and the compound 1-[4-(2-Amino-thiazol-4-yl)-phenyl]-pyrrole-2,5-dione (4a) which is a maleic derivative bearing thiazole ring, exhibited good anti-tubercular activity (MIC 6.25 μg/ml). Drug likeness was also evaluated for all the synthesised compounds using Molinspiration software. All synthesized compounds fulfilled the parameters of the Lipinski rule of five and showed drug-like properties. Through this study, it was proved that thiazole analogues have good anti-tubercular potentials.

An approach to "escape from flatland": Chemo-enzymatic synthesis and biological profiling of a library of bridged bicyclic compounds

A major reason for the low success rate in current drug development through chemical synthesis has been ascribed to the large fraction of quasi planar candidate molecules. Therefore, an "escape from flatland" strategy has been recommended for the generation of bioactive chemical entities. In a first attempt to test this recommendation, we synthesized a small collection of bridged bicyclic compounds possessing a rigid spherical core structure by combining a group of cyclic dienes with a collection of dienophiles. We started from planar biphenyl analogues and, by enzymatic dioxygenation, transformed them into hydroxylated diene structures. Using a small library of newly synthesized dienophiles, the dienes were converted into bridged bicycles via the Diels-Alder reaction. The resulting collection of 78 structures was first tested for bioactivity in a generic assay based on interference with the proliferation of mammalian cells. A more mechanism-targeted bioactivity profiling method, exploiting cellular impedance monitoring, was subsequently used to obtain suggestions for the mode of action exerted by those compounds that were the most active in the proliferation assay. Proteasome inhibition could be confirmed for 8 of a series of 9 respective candidates. Whilst 7 of these molecules showed relatively weak interference with proteasome activity, one candidate exerted a moderate but distinct inhibition. This result appears remarkable in view of the small size of the compound library, which was synthesized following a few basic considerations. It encourages the application of diverse synthetic approaches to further investigate the role of spherical shape for the success of compound libraries.

In-vitro cytotoxicity, antioxidant, bleomycin-dependent DNA damage and immunomodulatory evaluation of 1-(4-acetylphenyl)-3-aryloxypyrrolidine-2,5-dione based derivatives

A one pot, economical, and efficient synthesis of 1-(4-acetylphenyl)-3- aryloxypyrrolidine-2,5-diones-based derivatives 5a-l have been accomplished in single steps and in satisfactory yields from 1-(4-acetylphenyl)-pyrrole-2,5- diones 3 and phenols 4a-l. All the compounds were characterized by physical, spectroscopic, and elemental analysis. The selection of the bioassays was based on proving the drug receptor binding concept. Compounds 5g, 5k, 5h, 5i, 5a, and 5f showed the highest inhibitory antioxidant activity using ABTS methods. Compounds 5k, 5g, 5c, 5h, 5b, 5d, 5f, and 5j manifested the best protective effect against DNA damage induced by bleomycin. Moreover, an in-vitro cytotoxic activity evaluation of all synthesized compounds was against four cancer cell lines using 5-Fluorouracil as a standard anticancer drug. Springer Science+Business Media 2014.

Facile Michael-type addition of aromatic alcohols to N-(4-acetylphenyl) maleic imide

A one-pot, economical, and efficient synthesis of 1-(4-acetylphenyl)-3- aryloxypyrrolidine-2,5-diones has been accomplished in single steps and in satisfactory yields from 1-(4-acetylphenyl)-pyrrole-2,5-diones and aromatic alcohols. All the compounds were characterized by physical, spectroscopic, and elemental analysis.

Synthesis of 1-(4-((E)-3-arylacryloyl) phenyl)-3,4-dibromo-1Hpyrrole-2,5- diones and screening for anti-Candida and antituberculosis activity

A series of eleven 1-(4-((E)-3-arylacryloyl) phenyl)-3,4 dibromo-1H-pyrrole-2,5-diones (4′-aminochalcone- based dibromomaleimides) were synthesized using maleic anhydride and p-aminoacetophenone as starting material. Furthermore, there has been some additional work investigating the effect of these derivatives on biological activity. They were characterized using FTIR, 1H NMR, 13C NMR, ESI mass spectroscopy, and elemental analysis. The compounds show anti-Candida & antituberculosis activity.

Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore

Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.

Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions

DNA-encoded chemical libraries are increasingly being employed for the identification of binding molecules to protein targets of pharmaceutical relevance. Here, we describe the synthesis and characterization of a DNA-encoded chemical library, consisting of 4000 compounds generated by Diels-Alder cycloaddition reactions. The compounds were encoded with unique DNA fragments which were generated through a stepwise assembly process and serve as amplifiable bar codes for the identification and relative quantification of library members.