21835-60-9

Usage

Heterocyclic compound

Contains a nitrogen and oxygen atom within its five-membered ring structure

Aromatic nature

Can participate in various organic reactions

Uses

Building block in the synthesis of pharmaceuticals, dyes, and agrochemicals

Medicinal properties

Potential applications in the field of medicine and drug development

Upstream product

• 31604-39-4 2-(4-nitrophenyl)isoindoline-1,3-dione 
• 88-95-9 Phthaloyl dichloride 
• 106-50-3 1,4-phenylenediamine 
• 64-19-7 acetic acid 
• 85-44-9 phthalic anhydride 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 7677-24-9 trimethylsilyl cyanide 
• 88-67-5 2-Iodobenzoic acid 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 1218926-10-3 N-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]pyridine-2-carboxamide 
• 106075-85-8 4-methoxy-N-[4-(1,3-dioxoisoindolin-2-yl)phenyl]benzamide 
• 40101-24-4 N-[4-(1,3-dioxoisoindolin-2-yl)phenyl]benzamide 
• 27746-16-3 2-(4-(dimethylamino)phenyl)isoindoline-1,3-dione 
• 1427449-90-8 N-(4-(1,3-dioxoisoindolin-2-yl)phenyl)-4-pentenamide 
• 1427449-79-3 2-(4-(2-(fluoromethyl)-5-oxopyrrolidin-1-yl)phenyl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides

An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.

Discovery of phthalimide derivatives as novel inhibitors of a soluble epoxide hydrolase

Soluble epoxide hydrolase (sEH) inhibitors are effective in reducing blood pressure, inflammation, and pain in a number of mammalian disease models. As most classical urea-based sEH inhibitors suffer from poor solubility and pharmacokinetic properties, the development of novel sEH inhibitors with an improved pharmacokinetic specification has received a great deal of attention. In this study, a series of amide-based sEH inhibitors bearing a phthalimide ring as the novel secondary pharmacophore (P2) was designed, synthesized, and evaluated. Docking results illustrated that the amide group as the primary pharmacophore (P1) was placed at a suitable distance from the three key amino acids (Tyr383, Tyr466, and Asp335) for an effective hydrogen bonding. In agreement with these findings, most of the newly synthesized compounds demonstrated moderate?to?high sEH inhibitory activities, relative to 12-(3-adamantan-1-yl-ureido)dodecanoic acid as the reference standard. Compound 12e with a 4-methoxybenzoyl substituent exhibited the highest sEH inhibitory activity, with an IC50 value of 1.06 nM. Moreover, the ADME properties of the compounds were evaluated in silico, and the results revealed appropriate predictions.

Preparation method of bedaquiline and intermediate thereof

The invention discloses a preparation method of a bedaquiline racemate and a key intermediate compound used in the preparation method. According to the method for preparing the bedaquiline racemate, the ultra-low temperature reaction in the prior art is changed, and the ultra-low temperature reaction which is difficult to realize in the prior art is carried out at the conventional temperature, sothat large-scale industrialization becomes possible. Besides, the method provided by the invention greatly improves the conversion rate of the reaction substrate, improves the reaction yield, makes the product more easily crystallized and purified, and reduces the production cost at the same time.

PHTHALIMIDE DERIVATIVE METABOTROPIC GLUTAMATE R4 LIGANDS

Disclosed are mGluR4 positive allosteric modulator ligands of general formula (I) and radiolabeled derivates, their use as therapeutic agents for the treatment of central nervous system disorders modulated by mGluR4 and as ligands for the labeling and diagnostic imaging of mGluR4 in mammals.

Synthesis of hyperbranched aromatic poly(amide-imide): Copolymerization of B′B2 monomer with A2 monomer

A hyperbranched aromatic poly(amide-imide) was prepared by the copolymerization of 4-(3,5-dicarboxyphenoxy)phthalic anhydride, a B′B2type monomer, and 1,4-phenylenediamine, an A2 type monomer. The rapid reaction between the anhydride and amino group led to the formation of the dominant imide intermediate which can be regarded as a new AB2 type of monomer. The intermediate, without isolation, was subjected to further polymerization in the presence of TPP/pyridine, as condensing agents, to give the hyperbranched poly(amide-imide), containing carboxylic acid chain ends. In comparison, the AB2 monomer was prepared separately, and the conventional self-polymerization of this monomer was also studied. The structures of the obtained polymers were characterized by FTIR and 1H NMR spectroscopy. The spectral data showed that these two polymers, prepared from two different synthetic approaches, have nearly identical structures. The degree of branching of the hyperbranched poly(amide - imide)s was estimated to be 60-61%. The terminal carboxylic acid groups were modified by reaction with a variety of aromatic amines to give the corresponding amide derivatives. The nature of the chain ends was shown to have a significant effect on the solubility and Tg of the hyperbranched poly(amide-imide)s.

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.

The reduction of aromatic nitro compounds by oxiranes

Aromatic nitro compounds are reduced to the corresponding amines by epoxides at elevated temperatures (>170 deg C). - Key words: nitro compounds, amines, epoxides, reduction.