24870-12-0

Usage

Uses

Used in Organic Synthesis:
3-(N-(4-ACETYLPHENYL)CARBAMOYL)PROP-2-ENOIC ACID is used as a building block for the synthesis of various organic compounds. Its unique structure allows it to be a versatile intermediate in the creation of complex organic molecules.
Used in Medicinal Chemistry:
3-(N-(4-ACETYLPHENYL)CARBAMOYL)PROP-2-ENOIC ACID is used as a starting material for the development of new pharmaceuticals. Its potential biological activities make it a promising candidate for the discovery of novel therapeutic agents.
Used in Research and Development:
3-(N-(4-ACETYLPHENYL)CARBAMOYL)PROP-2-ENOIC ACID is used as a research tool in the study of chemical reactions and mechanisms. Its reactivity and structural features provide valuable insights into the behavior of similar compounds in various chemical processes.
Used in Pharmaceutical Industry:
3-(N-(4-ACETYLPHENYL)CARBAMOYL)PROP-2-ENOIC ACID is used as a key component in the formulation of new drugs. Its potential therapeutic properties make it a valuable asset in the development of innovative treatments for various diseases and conditions.

InChI:InChI=1/C12H11NO4/c1-8(14)9-2-4-10(5-3-9)13-11(15)6-7-12(16)17/h2-7H,1H3,(H,13,15)(H,16,17)/b7-6+

Upstream product

• 108-31-6 maleic anhydride 
• 99-92-3 p-aminobenzophenone 
• 627-63-4 fumaryl dichloride 

Downstream Products

• 569646-63-5 (Z)-3-{4-[(E)-(3-Phenyl-acryloyl)]-phenylcarbamoyl}-acrylic acid 
• 883309-71-5 Methyl N-(4-acetylphenyl)maleamate 
• 19990-28-4 5-(4-acetylphenylimino)-5H-furan-2-one 
• 1082-85-5 1-(4-acetylphenyl)-1H-pyrrole-2,5-dione 

Relevant academic research and scientific papers

Electrochemical and spectroscopic investigations of carboxylic acid ligand and its triorganotin complexes for their binding with ds.DNA: In vitro biological studies

A carboxylic acid ligand, (Z)-4-(4-acetylphenylamino)-4-oxobut-2-enoic acid (APA-1), and its triphenyl-(APA-2) and tributyl-tin(IV) (APA-3) compounds have been synthesized and investigated for their binding with ds.DNA using UV-visible spectroscopy, fluor

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.

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.

INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE

Correlation relationships describing the influence of substituents and solvents on the rate of acylation of aromatic amines and their polymeric analogs with maleic anhydride have been derived.