59208-49-0

Usage

Heterocyclic compound

isoindole ring and pyridine ring
The compound is a heterocyclic compound, containing both an isoindole ring (a benzene ring fused with a lactam ring) and a pyridine ring (a six-membered aromatic ring with one nitrogen atom).

Versatile chemical properties

used in synthesis of pharmaceuticals and agrochemicals
The compound's versatile chemical properties make it suitable for the synthesis of various pharmaceuticals and agrochemicals, contributing to its wide range of potential applications.

Antifungal properties

potential for drug development
The compound exhibits antifungal properties, making it a potential candidate for the development of new antifungal drugs.

Anti-inflammatory properties

potential for therapeutic applications
The compound also has anti-inflammatory properties, which could make it useful in the treatment of inflammation-related conditions.

Corrosion inhibitor

potential for metal surface protection
The compound has been studied for its potential role as a corrosion inhibitor for metal surfaces, which could have applications in materials science and engineering.

Upstream product

• 110-86-1 pyridine 
• 3481-09-2 N-chlorophthalimide 
• 504-29-0 2-aminopyridine 
• 85-44-9 phthalic anhydride 
• 5672-90-2 N-(trifluoromethyl)acyloxyphthalimide 
• 524-38-9 N-hydroxyphthalimide 

Downstream Products

• 19357-10-9 N-(2-pyridyl)-2-carboxybenzamide 
• 3532-41-0 3-hydroxy-3-phenyl-2-(pyridin-2-yl)isoindolin-1-one 
• 79419-92-4 3-(3-Chloro-phenyl)-3-hydroxy-2-pyridin-2-yl-2,3-dihydro-isoindol-1-one 
• 79419-91-3 3-(2-Chloro-phenyl)-3-hydroxy-2-pyridin-2-yl-2,3-dihydro-isoindol-1-one 
• 1574486-21-7 3-hydroxy-3-(4-methoxyphenyl)-2-(pyridin-2-yl)isoindolin-1-one 
• 1574486-22-8 3-(3,5-bis(trifluoromethyl)phenyl)-3-hydroxy-2-(pyridin-2-yl)isoindolin-1-one 
• 1026024-30-5 3,4-diphenyl-2-(pyridin-2-yl)isoquinolin-1(2H)-one 
• 79419-95-7 3-(2-Chloro-phenyl)-3-imidazol-1-yl-2-pyridin-2-yl-2,3-dihydro-isoindol-1-one 
• 79419-96-8 3-(3-Chloro-phenyl)-3-imidazol-1-yl-2-pyridin-2-yl-2,3-dihydro-isoindol-1-one 
• 77771-95-0 3-Imidazol-1-yl-3-phenyl-2-pyridin-2-yl-2,3-dihydro-isoindol-1-one 

Relevant academic research and scientific papers

Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides

The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.

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.

Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives

An environmentally friendly method is described for the synthesis of various isoindoline-1,3-dione derivatives from the reaction of phthalic anhydride with aromatic/aliphatic amines in ethanol at 80 °C by phthalimide-N-sulfonic acid as an efficient heterogeneous acid catalyst. Some advantages include the metal-free and environmentally friendly protocol, simple operation and reusable processes, easy recovery, short reaction times, and high yields.

Thalidomide analogues: Tumor necrosis factor-alpha inhibitors and their evaluation as anti-inflammatory agents

A series of related thalidomide derivatives (2-9) were synthesized by microwave irradiation and evaluated for anti-inflammatory activity. Such activity was assessed in vivo and ex vivo. Compounds 2, 8 and 9 showed the highest levels of inhibition of TNF-α production. On rat paw edema and hyperalgesia assays, compound 9, (1,4-phthalazinedione) demonstrated the highest in vivo anti-inflammatory activity. Thus, compound 9 can be considered as a promising compound to be subjected to further modification to obtain new agents for the treatment of inflammatory diseases.

N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes

This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.

Efficient synthesis of aryl hydroxylactams by reducing imides with activated zinc dust

A series of aryl hydroxylactams (2a, 2b, 2d-2g, 2i-2k, 2m, and 2n) was synthesized by partially reducing aryl cyclic imides in moderate to excellent yields with activated zinc dust alone in acetic acid. This method was regiospecific and can be employed as an alternative for reported methods to partially reduce aryl cyclic imides. Copyright Taylor & Francis Group, LLC.

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).