34403-39-9

Basic information

• Product Name: 2-(4-pyridinylmethyl)-1H-Isoindole-1,3(2H)-dione
• Synonyms: 2-(4-pyridinylmethyl)-1H-Isoindole-1,3(2H)-dione
• CAS NO: 34403-39-9
• Molecular Weight: 238.246
• Mol File: 34403-39-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(4-pyridinylmethyl)-1H-Isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-pyridinylmethyl)-1H-Isoindole-1,3(2H)-dione(34403-39-9)
• EPA Substance Registry System: 2-(4-pyridinylmethyl)-1H-Isoindole-1,3(2H)-dione(34403-39-9)

Safety Data

• Hazardous Substances Data: 34403-39-9(Hazardous Substances Data)

Usage

General Description

2-(4-pyridinylmethyl)-1H-Isoindole-1,3(2H)-dione, also known as EPL-1, is a chemical compound that belongs to the class of isoindolinone derivatives. It is a potent and selective inhibitor of the enzyme phosphodiesterase 10A (PDE10A), which plays a role in regulating the levels of intracellular signaling molecules like cAMP and cGMP. PDE10A inhibitors have potential therapeutic applications in the treatment of neurological and psychiatric disorders, such as schizophrenia and Huntington's disease. EPL-1 has shown promising results in preclinical studies for the treatment of these conditions, and it is a subject of ongoing research for its potential use as a pharmaceutical agent.

Upstream product

• 3731-53-1 4-(aminomethyl)pyridine 
• 85-44-9 phthalic anhydride 

Downstream Products

• 3731-53-1 4-(aminomethyl)pyridine 
• 1191083-53-0 [Au(PPh₃)(4-aminomethyl-N-phthalimidopyridine)](OTf) 

Relevant articles and documents

Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement

An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.

New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors

This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-α (TNFα) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and β-picolyl), allowing significant inhibition of TNFα production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNFα production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 μM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg-1) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 μM kg-1) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 μM kg-1).

(N-phthalimidoalkyl) piperidines useful as treatments for psychosis

There is described novel (N-phthalimidoalkyl) piperidine compounds which exhibit selective sigma-receptor antagonism and therefore are useful in the treatment of physiological or drug induced psychosis and dyskinesia in a mammal. Also described are pharmaceutical compositions containing sigma selective compounds and methods of using these compositions for treating physiological or drug induced psychosis or dyskinesia in a mammal. Further provided are methods for preparing the compounds of this invention.