40349-49-3

Usage

InChI:InChI=1/C12H9NO4/c1-17-12(16)8-2-4-9(5-3-8)13-10(14)6-7-11(13)15/h2-7H,1H3

Upstream product

• 67-56-1 methanol 
• 29305-46-2 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride 
• 125407-30-9 (Z)-4-((4-(methoxycarbonyl)phenyl)amino)-4-oxobut-2-enoic acid 
• 150-13-0 4-amino-benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 
• 108-31-6 maleic anhydride 
• 17057-04-4 N-(4-carboxyphenyl)maleimide 
• 74-88-4 methyl iodide 

Downstream Products

• 339090-38-9 Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate 
• 1229020-49-8 C₃₁H₄₅N₃O₅ 

Relevant academic research and scientific papers

Biologically active thio-pyrimidinones from base-catalyzed thiol-ene coupling with maleimides

The synthesis of 2-thiopyrimidinones through thiol-ene coupling is reported here, resulting in 35 unpublished molecules. Thiopyrimidinones may exhibit one up to three tautomeric forms, and favoring the thiol tautomer is favored is the key to success of this reaction. Five compounds from all obtained products, those substituted with a carbonyl ester portion in the side chain, were chosen to be tested in a preliminary evaluation for human aldose reductase inhibition. All tested compounds showed an inhibition percentage equal to or >60%.

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.

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.).

Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives

In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR,1H NMR,13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.

Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis

Synthesis of highly substituted quinolines has been developed based on three-component radical cascade based on visible-light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron-rich β-aminoacrylates with electron-deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described. (Figure presented.).

Discovery and structural optimization of pyrazole derivatives as novel inhibitors of Cdc25B

Structural optimization and preliminary structure-activity relationship studies of a series of N-substituted maleimide fused-pyrazole analogues with Cdc25B inhibitory activity, starting from a high-throughput screening hit, are illustrated. A simplified 3,5-diacyl pyrazole analogue was obtained as the most potent compound (118, IC50 = 0.12 μM) with a 270-fold increase in potency.

4-(3-Dialkylamino-2,5-dioxopyrrolidin-1-yl)benzoic acid esters

Reactions of alkyl 4-aminobenzoates with maleic anhydride give the corresponding alkyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoates, and the latter are converted into 4-(3-dialkylamino-2,5-dioxo-2,3,4,5-tetrahydro-1H- pyrrol-1-yl)benzoates by treatme

Investigation of arene-arene interaction in stereoselective MCPBA epoxidation

Effect of arene-arene interaction in stereoselective MCPBA epoxidation was investigated using 5,6-dimethyl-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-diones 1. From the good correlation between the stereoselectivity of the products and Hammett's coefficients of para-substituents (σP) on the phenyl group, it was found that polar/π interaction between the phenyl group and MCPBA is the main interaction for controlling the stereoselectivity in the reaction. Other arene-arene interactions, charge-transfer complexation and edge-to-face interaction, were assumed to be much weaker than polar/π interaction in this reaction.

Compounds containing a michael-acceptor, especially maleimide or maleic acid derivatives, directly or indirectly linked to a chromophore and their use in long lasting sunscreen compositions

The present invention relates to compounds which are useful as sunscreens. The compounds persist on the skin for much longer than conventional sunscreens because they comprise a Michael acceptor linked directly or indirectly to a chromophore. The Michael acceptor is capable of undergoing a conjugate addition reaction with thiol groups present in cysteine residues of keratin and thus the compound is chemically bound to the skin and will not be removed by immersion in water.