112749-49-2

Usage

Structure

1H-Pyrrole-2,5-dione core with a bromine atom attached to the third carbon, and a phenylmethyl group attached to the first carbon

Type

Brominated derivative of 1-(phenylmethyl)pyrrole-2,5-dione

Usage

Organic building block in the synthesis of pharmaceutical and agrochemical compounds

Applications

Medicinal chemistry, drug discovery research, and further functionalization of the molecule for various applications in organic synthesis.

Upstream product

• 108-31-6 maleic anhydride 
• 100-46-9 benzylamine 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 91026-00-5 N-benzyl-2,3-dibromo-maleimide 
• 5926-51-2 bromomaleic anhydride 

Downstream Products

• 853649-60-2 3-[5-(diethoxymethyl)fur-2-yl]-2,5-dihydro-1-benzyl-1H-pyrrole-2,5-dione 
• 935525-82-9 1-benzyl-3-isobutyl-pyrrole-2,5-dione 
• 1013400-89-9 C₁₄H₁₅NO₄ 
• 897036-92-9 1-benzyl-3-methoxy-1H-pyrrole-2,5-dione 
• 1206838-03-0 C₁₆H₁₄BrNO₂ 
• 1206838-11-0 C₁₇H₁₆BrNO₂ 
• 1353013-52-1 1-benzyl-3-(hex-1-yn-1-yl)-1H-pyrrole-2,5-dione 
• 16213-29-9 1-benzyl-3-p-tolyl-1H-pyrrole-2,5-dione 

Relevant academic research and scientific papers

Copper-catalysed bromoamination of maleimides using NBS as the bromine source

CuBr2-catalysed bromoamination of maleimides has been achieved in THF with alkylamines and N-bromosuccinimide as nitrogen and bromine sources respectively. The reaction conditions were optimised. A series of bromoamination products such as 3-am

Easy Access to 1H-Pyrrolo[3′,4′:5,6]pyrido[2,3-d]pyrimidine-2,4,6,8(3H,7H)-tetraone and Selectively N7-Substituted Analogues through Key Synthons

To synthesize unsubstituted pyrrolo[3′,4′:5,6] pyrido[2,3-d]pyrimidine-2,4,6,8-tetraone, we have developed new synthon 4-formyl-3-hydroxy-2,5-dioxo-2,5-dihydro-1H-pyrrole, which was then treated under mild conditions with 6-aminouracil. This new synthetic pathway could be extended to the preparation of N7-selectively substituted heterocycles by starting either from this new synthon or from its N-substituted analogues. Examples of N1,N7-disubstituted and N1,N3,N7-trisubstituted derivatives are also described. We have thus developed new synthons that lead to easy access to the unsubstituted pyrrolo[3′,4′:5,6]pyrido[2,3-d]pyrimidine-2,4,6,8-tetraone skeleton and to selectively N7-substituted analogues. New key synthons, 4-formyl-3-hydroxy-2,5-dioxo-2,5-dihydro-1H-pyrrole and its N-substituted analogues, have been developed for easy and versatile syntheses of heterocyclic skeletons, such as unsubstituted pyrrolo[3′,4′:5,6]pyrido[2,3-d]pyrimidine-2,4,6,8-tetraone.

Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds

The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C-C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.

Electrochemical synthesis method of 3,4-dibromomalayimide

The present invention relates to the field of organic synthesis technology, in particular to a 3,4-dibromo maleimide electrochemical synthesis method, maleimide as the starting material, to inexpensive, safe and readily available bromide as a bromine sour

A mild and selective protecting and reversed modification of thiols

One selective thiol-protecting study has been investigated for a wide range of thiols including general thiols and thiols containing multiple functional groups. The reactions of bromomaleimides and thiols under the mild condition afforded the protected products in excellent yields. The thiols can be recovered very quickly using dithiothreitol (DTT) under the mild condition.

Small molecule inhibitors of regulators of G protein signaling (rgs) proteins

Recently, regulators of G protein signaling (RGS) proteins have emerged as potential therapeutic targets since they provide an alternative method of modulating the activity of G protein-coupled receptors, the target of so many drugs. Inhibitors of RGS proteins must block a protein-protein interaction (RGS-Gα) but also be cell and, depending on the therapeutic target, blood-brain barrier permeable. A lead compound (1a) was identified as an inhibitor of RGS4 in a screening assay, and this has now been optimized for activity, selectivity, and solubility. The newly developed ligands (11b and 13) display substantial selectivity over the closely related RGS8 protein, lack the off-target calcium mobilization activity of the lead 1a, and have excellent aqueous solubility. They are currently being evaluated in vivo in rodent models of depression.

SMALL MOLECULE INHIBITORS OF RGS PROTEINS

The invention relates to compositions having RGS (regulator of G-protein Signaling) inhibiting activity, and methods of use thereof. In some embodiments, RGS-inhibiting compositions find use in research on or treatment of disease states (e.g., diabetes, epilepsy, neuropathic pain, depression and other diseases)

First total synthesis of 5-hydroxy-3-methyl-4-propylsulfanyl-5 h -furan-2-one: A cancer chemopreventive agent

The first total synthesis of 5-hydroxy-3-methyl-4-propylsulfanyl-5H-furan- 2-one, a newly discovered natural product with anticancer property is described by two different routes. A sequence involving an incorporation of a methyl group via a Gilman reagent and a chemoselective reduction of a cyclic anhydride functionality are the key steps. The methods proposed start from easily available starting materials and allow ready preparation of the final compound in good overall yield. Georg Thieme Verlag Stuttgart · New York.

Highly Enantioselective diels-alder reactions of maleimides catalyzed by activated chiral oxazaborolidines

[Chemical equation presented] Diels-Alder reactions of various combinations of maleimides and 1,3-dienes with cationic oxazaborolidines as catalysts have been shown to be highly efficient and enantioselective.

A flexible approach to methyl (5S)-5-alkyltetramate derivatives

Regioselective Grignard reagent additions to 3-methoxymaleimides and subsequent diastereoselective reductive dehydroxylation of the resulting N,O-acetals were studied. On the basis of these studies, a flexible and highly regio- and diastereoselective approach to methyl 5-alkyltetramate derivatives was disclosed. The method is the first direct and flexible asymmetric cationic synthon-based approach, and allows for the synthesis of various methyl (5S)-5-alkyltetramate derivatives that are otherwise inaccessible by the commonly used methods based on α-amino acids. Georg Thieme Verlag Stuttgart.