33238-32-3

Usage

Chemical class

isoindole-1,3-diones

Structure

1H-isoindole-1,3(2H)-dione core with a 2-methyl-5-nitrophenyl substituent

Potential applications

pharmaceutical and medicinal chemistry

Biological activities

antimicrobial, anticancer, and anti-inflammatory properties

Research interest

synthesis and biological evaluation for drug discovery and chemical biology

Upstream product

• 85-44-9 phthalic anhydride 
• 99-55-8 2-methyl-5-nitroaniline 

Downstream Products

• 92437-60-0 N-(5-amino-2-methyl-phenyl)-phthalimide 

Relevant academic research and scientific papers

Synthesis, molecular docking, cytotoxicity and antioxidant activity evaluation of isoindoline-1,3-dione derivatives

A variety of amines have been employed to functionalize isobenzofuran-1,3-dione to obtain isoindoline-1,3-dione derivatives in the base free conditions. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa) and antioxidant activity. ABTS and DPPH are employed to assess the antioxidant activity. Among the synthesized isoindoline-1,3-dione derivatives (3a-k), compound 3e has showed the best antioxidant activity and also exhibited better binding energy when docked with caspase-3 protein. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa) and compound 3e has displayed better activity than other isoindoline derivatives.

Synthesis and anticonvulsant and neurotoxic properties of substituted N- phenyl derivatives of the phthalimide pharmacophore

A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4- nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-mitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2- methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro- 4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3- amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal (ip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED50 values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC50 values for 17 and phenytoin were 0.15 and 0.93 μM, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED50 values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 μM excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltagegated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.