37597-19-6

Usage

Chemical group

Pyrrole-2,5-dione

Structural feature

Contains a dimethoxy-phenyl-ethyl moiety

Molecular weight

273.28 g/mol

Application

Important building block in organic synthesis

Industries

Potential applications in pharmaceutical and agrochemical industries

Pharmacological properties

Known for its pharmacological properties

Therapeutic effects

Studied for its potential therapeutic effects

Other uses

May have uses in material science and other industrial applications

InChI:InChI=1/C14H15NO4/c1-18-11-4-3-10(9-12(11)19-2)7-8-15-13(16)5-6-14(15)17/h3-6,9H,7-8H2,1-2H3

Upstream product

• 617-48-1 malic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 108-31-6 maleic anhydride 

Downstream Products

• 446063-58-7 (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide 
• 446063-56-5 (2R,6S)-4-[2-(3,4-dimethoxyphenyl)ethyl]-2-[(1S,2R,4R,S_R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfinyl]-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 446063-61-2 (1R,2R,6S,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-5-methyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 446063-64-5 (1R,2R,6S,7S)-5-Butyl-4-[2-(3,4-dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 712019-97-1 (1R,2S,6R,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-5-methylene-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 712016-55-2 (1R,2R,6S,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 712018-62-7 (2R,6S)-(-)-2-[(1S,2R,4R,S_R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfinyl]-4-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 446063-59-8 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-pyrrole-2,5-dione 

Relevant academic research and scientific papers

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.

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).

Direct synthesis of imides from dicarboxylic acids using microwaves

1,4- and 1,5-dicarboxylic acids, when treated with amines in a domestic microwave oven, afford good yields of the corresponding imides.

Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones

A procedure for producing 1,4-dianion equivalents consists of reductive lithiation, induced by 4,4-di-tert-butylbiphenylide, of functionalized phenyl sulfides. Nucleophilic addition of 4-lithio-2-(trimelhylsilylmethyl)but-1- ene 1 and 2-(3-lithiopropyl)-2