73328-71-9

Basic information

• Product Name: 1-(2,6-DICHLORO-4-HYDROXPHENYL)-1,3-DIHYDROINDOL-2-ONE
• Synonyms: 1-(2,6-DICHLORO-4-HYDROXPHENYL)-1,3-DIHYDROINDOL-2-ONE;1-(2,6-Dichloro-4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one
• CAS NO: 73328-71-9
• Molecular Formula: C₁₄H₉Cl₂NO₂
• Molecular Weight: 280.14924
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 73328-71-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Very Slightly)
• CAS DataBase Reference: 1-(2,6-DICHLORO-4-HYDROXPHENYL)-1,3-DIHYDROINDOL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-DICHLORO-4-HYDROXPHENYL)-1,3-DIHYDROINDOL-2-ONE(73328-71-9)
• EPA Substance Registry System: 1-(2,6-DICHLORO-4-HYDROXPHENYL)-1,3-DIHYDROINDOL-2-ONE(73328-71-9)

Safety Data

• Hazardous Substances Data: 73328-71-9(Hazardous Substances Data)

Usage

Description

1-(2,6-Dichloro-4-hydroxyphenyl)-1,3-dihydroindol-2-one, with the CAS number 73328-71-9, is an organic compound that plays a significant role in various chemical reactions and processes. Its unique molecular structure, featuring a dichloro-hydroxyphenyl group and a dihydroindolone core, endows it with specific properties that make it valuable in the field of organic synthesis.

Uses

Used in Organic Synthesis:
1-(2,6-Dichloro-4-hydroxyphenyl)-1,3-dihydroindol-2-one is used as a key intermediate in the synthesis of various organic compounds. Its application in this field is primarily due to its ability to participate in a range of chemical reactions, such as substitution, addition, and condensation, which can lead to the formation of diverse and complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(2,6-Dichloro-4-hydroxyphenyl)-1,3-dihydroindol-2-one is used as a building block for the development of new drugs. Its unique chemical properties allow it to be incorporated into the molecular structures of potential therapeutic agents, which can then be further modified and optimized for specific medical applications.
Used in Chemical Research:
1-(2,6-Dichloro-4-hydroxyphenyl)-1,3-dihydroindol-2-one is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic pathways. Its reactivity and structural features make it an ideal candidate for investigating the effects of different reaction conditions and catalysts on the outcome of chemical transformations.
Used in Material Science:
In the field of material science, 1-(2,6-Dichloro-4-hydroxyphenyl)-1,3-dihydroindol-2-one can be employed in the development of novel materials with specific properties. Its incorporation into polymeric structures, for instance, can lead to the creation of materials with enhanced mechanical, thermal, or electrical characteristics, depending on the desired application.

Upstream product

• 136099-58-6 N-[(2,6-dichloro-4-methoxy)phenyl]-N-phenyl chloroacetamide 
• 320778-04-9 1-(2,6-dichloro-4-methoxyphenyl)-isatin 
• 136099-56-4 N-Phenyl-(2,6-dichloro-4-methoxy)-aniline 
• 64118-84-9 4'-hydroxydiclofenac 
• 118409-80-6 2-[(2,6-dichloro-4-methoxyphenyl)amino]phenylacetic acid 

Downstream Products

• 64118-84-9 4'-hydroxydiclofenac 

Relevant articles and documents

Diclofenac toxicity to hepatocytes: A role for drug metabolism in cell toxicity

Diclofenac, a 2-arylacetic acid, nonsteroidal anti-inflammatory drug, has been reported to cause adverse hepatic effects in certain individuals. To discriminate among possible mechanisms of hepatotoxicity, we examined the effects of diclofenac on human and rat hepatocytes and hepatic cell lines (HepG2, FaO), investigated the major biochemical events in the course of diclofenac cytotoxicity (calcium homeostasis, lipid peroxidation, and mitochondrial dysfunction), and investigated whether cytotoxicity could be related to drug metabolism by cytochrome P-450. Acute diclofenac-induced toxicity in hepatocytes was preluded by a decrease in ATP levels, whereas no significant oxidative stress (decrease in glutathione and lipid peroxidation) or increase in intracellular calcium concentration could be observed at early incubation stages. Diclofenac was more cytotoxic to drug metabolizing cells (rat and human primary cultured hepatocytes) than to nonmetabolizing cell lines (HepG2, FaO). Despite the fact that diclofenac itself was effective in impairing ATP synthesis by mitochondria, we found evidence that toxicity was also related to drug metabolism and was reduced by the addition of cytochrome P-450 inhibitors (proadifen and ketoconazole) to culture medium. The in vitro cytotoxicity correlated well with the formation by hepatocytes of 5- hydroxydiclofenac and, in particular, N,5-dihydroxydiclofenac, a minor metabolite first characterized in this article. Hepatic microsomes showed the ability to both oxidize 5-hydroxydiclofenac to N,5-dihydroxydiclofenac and back reduce the latter to 5-hydroxydiclofenac with the consumption of NADPH. The experimental results suggest that the toxic effect of diclofenac on hepatocytes may be caused by drug-induced mitochondrial impairment, together with a futile consumption of NADPH.

Synthesis and quantitative structure-activity relationships of diclofenac analogues

The synthesis of a series of 2-anilinophenylacetic acid, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.