3975-50-6

Usage

Class

Isoindoles (heterocyclic compounds with a five-membered ring and two nitrogen atoms)

Contains a hydroxyl group

Gives alcohol properties

Contains a phenyl group

Gives aromatic properties

Used as a building block in the synthesis of pharmaceuticals and organic compounds

Due to its reactivity and versatile chemical properties

Potential applications

In the development of drugs and materials for various industries

Upstream product

• 610-35-5 4-hydroxyphthalic acid 
• 27550-59-0 4-hydroxyphthalic anhydride 
• 62-53-3 aniline 
• 941-69-5 N-phenyl-maleimide 
• 203728-19-2 2-(2-Oxo-2H-pyran-4-yloxy)-isoindole-1,3-dione 

Downstream Products

• 19048-25-0 5-hydroxy-2-phenylisoindolin-1-one 
• 1260224-92-7 4-chloro-3'-((1-oxo-2-phenylisoindolin-5-yloxy)methyl)biphenyl-3-carboxylic acid 
• 1260225-03-3 C₂₉H₂₂ClNO₄ 
• 1242154-46-6 2-phenylisoindole-1,3-dion-5-yl (E)-3-(4-nitrophenyl)acrylat 
• 147810-07-9 trifluoro-methanesulfonic acid 1,3-dioxo-2-phenyl-2,3-dihydro-1H-isoindol-5-yl ester 

Relevant academic research and scientific papers

Design and synthesis of an orally active metabotropic glutamate receptor subtype-2 (mGluR2) positive allosteric modulator (PAM) that decreases cocaine self-administration in rats

The modification of 3′-((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3- dihydro-1H-inden-5-yloxy)methyl)biphenyl-4-carboxylic acid (BINA, 1) by incorporating heteroatoms into the structure and replacing the cyclopentyl moiety led to the development of new mGluR2 positive allosteric modulators (PAMs) with optimized potency and superior druglike properties. These analogues are more potent than 1 in vitro and are highly selective for mGluR2 vs other mGluR subtypes. They have significantly improved pharmacokinetic (PK) properties, with excellent oral bioavailability and brain penetration. The benzisothiazol-3-one derivative 14 decreased cocaine self-administration in rats, providing proof-of-concept for the use of mGluR2 PAMs for the treatment of cocaine dependence.

Development of tryptase inhibitors derived from thalidomide

A novel series of tryptase inhibitors with a N-phenylphthalimide skeleton structurally derived from thalidomide (1) has been developed. Structure-activity relationship studies led to a potent and selective tryptase inhibitor, 2-(4-cyanophenyl)isoindole-1,3-dione-5-yl 3-(2-aminopyridin-5-yl)propanoate (7), with the IC50 value of 78 nM.

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 and reactivity of a novel group of hydroxylamine-containing 2π- and 4π-components

The synthesis of hydroxylamine-based reagents, alkene 2, alkyne 3 and a butadienyl variant pyrone 4 are described. While the relative instability of alkyne 3 has limited further evaluation, alkene 2 and pyrone 4 successfully participate in 1,3-dipolar and Diels-Alder cycloaddition reactions respectively. Reaction of 4 with DMAD gives O-arylated hydroxylamine 13, the structure of which is confirmed by crystallographic analysis.