67822-75-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Benzyl-1,3-dioxoisoindoline-5-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 2-benzyl-1,3-dioxoisoindoline-5-carboxylic acid is employed as a reactant in the synthesis of diverse organic compounds. Its reactivity and functional groups make it suitable for creating complex molecules with specific properties.
Used in Chemical Research and Development:
2-Benzyl-1,3-dioxoisoindoline-5-carboxylic acid serves as a valuable tool in chemical research and development. Its unique properties and reactivity enable scientists to explore new chemical reactions and pathways, potentially leading to the discovery of innovative materials and compounds.

InChI:InChI=1/C16H11NO4/c18-14-12-7-6-11(16(20)21)8-13(12)15(19)17(14)9-10-4-2-1-3-5-10/h1-8H,9H2,(H,20,21)/p-1

Upstream product

• 1025907-99-6 2-Benzyl-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid benzylamide 
• 100-46-9 benzylamine 
• 552-30-7 trimellitic Anhydride 
• 780-25-6 N-benzylidene benzylamine 

Downstream Products

• 67822-79-1 2-benzylisoindolin-1,3-dione-5-carboxylic acid chloride 
• 868622-65-5 2-benzyl-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid tert-butoxy-amide 
• 914646-53-0 2-benzyl-3-oxoisoindoline-5-carboxylic acid 
• 914646-55-2 2-benzyl-3-oxoisoindoline-5-carbaldehyde 
• 914646-54-1 2-benzyl-6-(hydroxymethyl)isoindolin-1-one 
• 914646-56-3 (E)-methyl 3-(2-benzyl-1-oxoisoindolin-6-yl)acrylate 
• 914646-57-4 (E)-3-(2-benzyl-1-oxoisoindolin-6-yl)acrylic acid 
• 914646-58-5 (E)-3-(2-benzyl-1-oxoisoindolin-6-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide 
• 159718-63-5 2-benzyl-5-pentanoylisoindolin-1,3-dione 
• 159718-64-6 2-benzyl-5-pentyl-isoindolin-1,3-dione 
• 1026257-68-0 2-benzyl-5-acetylisoindolin-1,3-dione 
• 1027511-63-2 2-Benzyl-5-ethyl-isoindole-1,3-dione 
• 868622-72-4 2-(2-benzyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-ylmethyl)-malonic acid dimethyl ester 
• 868622-73-5 3-(2-benzyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)-propionic acid 

Relevant academic research and scientific papers

Synthesis and anti-inflammatory activity of sulfonamides and carboxylates incorporating trimellitimides: Dual cyclooxygenase/carbonic anhydrase inhibitory actions

Trimellitimides 6–21 were prepared and investigated in vivo for anti-inflammatory and ulcerogenic effects and in vitro for cytotoxicity. They were subjected to in vitro cyclooxygenase (COX-1/2) and carbonic anhydrase inhibition protocols. Compounds 6–11 a

Pyrazole-isoindoline-1,3-dione hybrid: A promising scaffold for 4-hydroxyphenylpyruvate dioxygenase inhibitors

The discovery of 4-hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) inhibitors has been an active area of research due to their great potential as herbicides for weed control. Starting from the binding mode of known inhibitors of HPPD, a series of HPPD inhibitors with new molecular scaffolds were designed and synthesized by hybridizing 2-benzoylethen-1-ol and isoindoline-1,3-dione fragments. The results of the in vitro tests indicated that the newly synthesized compounds showed good HPPD inhibitory activity with IC50 values against the recombinant Arabidopsis thaliana HPPD (AtHPPD) ranging from 0.0039 ?M to over 1 ?M. Most promisingly, compound 4ae, 2-benzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)isoindoline-1,3-dione, showed the highest AtHPPD inhibitory activity with a Ki value of 3.92 nM, making it approximately 10 times more potent than pyrasulfotole (Ki = 44 nM) and slightly more potent than mesotrione (Ki = 4.56 nM). In addition, the cocrystal structure of the AtHPPD-4ae complex was successfully resolved at a resolution of 1.8 ?. The X-ray diffraction analysis indicated that the two carbonyl groups of 2-benzoylethen-1-ol formed a bidentate chelating interaction with the metal ion, while the isoindoline-1,3-dione moiety formed pronounced π-π stacking interactions with Phe381 and Phe424. Moreover, water-mediated hydrogen bonding interactions were observed between Asn282 and the nitrogen atoms of the pyrazole ring of 4ae. The above results showed that the pyrazole-isoindoline-1,3-dione hybrid is a promising scaffold for developing HPPD inhibitors.

An expedient method to the synthesis of N-substituted 1H-isoindole-1,3(2H)- diones

The synthesis of N-substituted 1H-isoindole-1,3-(2H)-diones is described from the reaction of cyclic anhydrides with Schiff bases as suitable replacing substrates instead of the corresponding amines. The Japan Institute of Heterocyclic Chemistry.

Design, synthesis, and biological evaluation of 1,3-dioxoisoindoline-5-carboxamide derivatives as T-type calcium channel blockers

A small molecule library of 1,3-dioxoisoindoline-5-carboxamides 4 was designed based on the pharmacophore model, synthesized and biologically evaluated as potential T-type calcium channel blockers. The most active compounds 4d and 4n show T-type calcium c

Design and synthesis of phthalimide-type histone deacetylase inhibitors

Several hydroxamic acid derivatives with a substituted phthalimide group as a linker and/or cap structure, prepared during structural development studies based on thalidomide, were found to have histone deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that nature of the substituent introduced at the phthalimide nitrogen atom, introduction of a hydroxamic acid structure, and distance between the N-hydroxyl group and the cap structure are important for HDAC-inhibitory activity.

Synthesis of isotopically-labelled nitroxyl radicals for use as spin probes

The synthesis of [15N]-1,1,3,3-tetrakis(trideuteriomethyl)isoindolin-2-yloxyl and of some 5-alkyl derivatives have been achieved by standard synthetic routes. The presence of deuterium improves the sharpness of the signals, and this, together with the incorporation of nitrogen-15, enhances the application of such compounds as spin probes; allyl substituents at C-5 improve the lipophilicity.