82585-50-0

Usage

Molecular weight

353.32 g/mol

Chemical structure

1H-Isoindole-1,3(2H)-dione, 2-[2-(4-fluorophenyl)-2-oxoethyl]-

Appearance

Yellow crystalline solid

Solubility

Practically insoluble in water, slightly soluble in ethanol, soluble in methanol and dimethyl sulfoxide (DMSO)

Anti-inflammatory properties

Tryptanthrin has been shown to reduce inflammation by inhibiting the production of pro-inflammatory mediators such as prostaglandins and leukotrienes.

Anti-cancer properties

Tryptanthrin has been found to inhibit the growth of cancer cells by interfering with cell division and inducing apoptosis (programmed cell death).

Anti-microbial properties

Tryptanthrin has demonstrated activity against various microorganisms, including bacteria, fungi, and viruses, by disrupting their cell membranes and inhibiting essential enzymes.

Research studies

Tryptanthrin has been the subject of various research studies for its potential therapeutic applications, including its ability to inhibit the growth of cancer cells, reduce inflammation, and combat microbial infections.

Pharmaceutical development

Tryptanthrin is a promising candidate for further development as a pharmaceutical agent for various medical conditions, including cancer, inflammatory diseases, and infectious diseases.

Upstream product

• 1074-82-4 potassium phtalimide 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 136918-14-4 phthalimide 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 85-44-9 phthalic anhydride 

Downstream Products

• 1286255-66-0 4-bromo-N-[2-(4-fluorophenyl)allyl]benzamide 
• 106191-62-2 β-(4-fluorophenyl)-β-methyleneethanamine 
• 1017172-13-2 2-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-isoindole-1,3-dione 
• 456-05-3 2-amino-1-(4-fluorophenyl)ethanol 
• 1607823-30-2 C₂₆H₂₆FNO₆S₂ 
• 1607823-21-1 C₁₆H₉BrFNO₃ 
• 1607823-25-5 S-1-(1,3-dioxoisoindolin-2-yl)-2-(4-fluorophenyl)-2-oxoethyl O-ethyl carbonodithioate 
• 1253734-03-0 2-[2-dimethylamino-1-(4-fluorobenzoyl)-vinyl]isoindole-1,3-dione 
• 456-00-8 2-amino-4'-fluoroacetophenone hydrochloride 

Relevant academic research and scientific papers

Dual Parasiticidal Activities of Phthalimides: Synthesis and Biological Profile against Trypanosoma cruzi and Plasmodium falciparum

Chagas disease and malaria are two neglected tropical diseases (NTDs) that prevail in tropical and subtropical regions in 149 countries. Chagas is also present in Europe, the US and Australia due to immigration of asymptomatic infected individuals. In the absence of an effective vaccine, the control of both diseases relies on chemotherapy. However, the emergence of parasite drug resistance is rendering currently available drugs obsolete. Hence, it is crucial to develop new molecules. Phthalimides, thiosemicarbazones, and 1,3-thiazoles have been used as scaffolds to obtain antiplasmodial and anti-Trypanosoma cruzi agents. Herein we present the synthesis of 24 phthalimido-thiosemicarbazones (3 a–x) and 14 phthalimido-thiazoles (4 a–n) and the corresponding biological activity against T. cruzi, Plasmodium falciparum, and cytotoxicity against mammalian cell lines. Some of these compounds showed potent inhibition of T. cruzi at low cytotoxic concentrations in RAW 264.7 cells. The most active compounds, 3 t (IC50=3.60 μM), 3 h (IC50=3.75 μM), and 4 j (IC50=4.48 μM), were more active than the control drug benznidazole (IC50=14.6 μM). Overall, the phthalimido-thiosemicarbazone derivatives were more potent than phthalimido-thiazole derivatives against T. cruzi. Flow cytometry assay data showed that compound 4 j was able to induce necrosis and apoptosis in trypomastigotes. Analysis by scanning electron microscopy showed that T. cruzi trypomastigote cells treated with compounds 3 h, 3 t, and 4 j at IC50 concentrations promoted changes in the shape, flagella, and surface of the parasite body similar to those observed in benznidazole-treated cells. The compounds with the highest antimalarial activity were the phthalimido-thiazoles 4 l (IC50=1.2 μM), 4 m (IC50=1.7 μM), and 4 n (IC50=2.4 μM). Together, these data revealed that phthalimido derivatives possess a dual antiparasitic profile with potential effects against T. cruzi and lead-like characteristics.

Convergent routes to substituted naphthylamides

Practical, convergent routes to variously substituted 1- and 2-naphthylamides have been developed. They exploit the ability of xanthates to undergo both intermolecular radical additions to vinyl pivalate and intramolecular radical cyclisations to aromatic

Efficient preparation of biologically important 1,2-amino alcohols

An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH 3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60C to yield biologically important 1,2-amino alcohols.

1-PYRAZOLO[4,3-C]ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF

The invention relates to a compound of formula (I), where: R1 is a phenyl group optionally substituted by one or more halogen atoms; R2 is: a hydrogen atom or a halogen atom or a cyano group; a —C(═O)Y group where Y is a hydrogen ato

The preparation and in vitro antiproliferative activity of phthalimide based ketones on MDAMB-231 and SKHep-1 human carcinoma cell lines

The 'one pot' condensation reaction for the synthesis and potent antiproliferative inhibition of α-phthalimide based ketones is reported here. 2-Phthalimide-1-(4-fluoro-phenyl)ethanone (5) showed the best growth inhibition on human MDAMB-231 breast carcin

INDOLE-2-CARBOXYLIC ACID AMIDES

Compounds represented by Formula (I) or pharmaceutically acceptable salts thereof, are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or

Palladium-catalyzed asymmetric hydrogenation of functionalized ketones

(Chemical Equation Presented) A novel catalytic system for asymmetric hydrogenation of functionalized ketones has been developed using a Pd/bisphosphine complex as the catalyst in 2,2,2-trifluoroethanol. The reaction exhibits high enantioselectivity, and

Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines

Convenient syntheses of 1H-pyrazin-2-ones and 2-aminopyrazines are described. By coupling Boc-protected amino acids with α-amino ketones or with amino alcohols and subsequent oxidation, 1H-pyrazin-2-ones were obtained. Transformation into the corresponding pyrazine triflates and substitution with primary or secondary amines led to 2-aminopyrazines. Since these syntheses take advantage of the use of readily available starting materials (e.g., amino acids, aminoalcohols and amines) a variety of the entitled structures can be obtained in few, high yielding steps.

Highly Enantioselective Asymmetric Hydrogenation of α-Phthalimide Ketone: An Efficient Entry to Enantiomerically Pure Amino Alcohols

A new type of α-phthalimide ketones was hydrogenated in excellent enantioselectivity by using a Ru-(C3-TunePhos) complex as the catalyst. Up to 10000 turnovers have been achieved in more than 99% ee in the hydrogenation reaction. A dynamic kinetic resolution study for the synthesis of threonine was performed, and high anti selectivity (>97:3) was observed for the first time. An efficient method to synthesize enantiomerically pure amino alcohols has been developed. Copyright

PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDE INHIBITORS OF GLYCOGEN PHOSHORYLASE

Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are inhibitors of glycogen phosphorylase and are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.