102359-00-2

Basic information

• Product Name: 5-CARBOXYOXINDOLE
• Synonyms: 5-CARBOXYOXINDOLE;RARECHEM AL BO 0983;OXINDOLE-5-CARBOXYLIC ACID;2-Oxo-indoline-5-carboxylic acid;5-CARBOXY-2-OXINDOLE;5-Carboxyoxindole 97%;2-Oxindole-5-carboxylic acid;2-Oxindole-5-carboxylic a...
• CAS NO: 102359-00-2
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• Product Categories: blocks;Carboxes;IndolesOxindoles;Indoline & Oxindole
• Mol File: 102359-00-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 310-316°C
• Boiling Point: 459.8 °C at 760 mmHg
• Flash Point: 231.9 °C
• Appearance: /
• Density: 1.433 g/cm³
• Vapor Pressure: 2.99E-09mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 4.19±0.20(Predicted)
• CAS DataBase Reference: 5-CARBOXYOXINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CARBOXYOXINDOLE(102359-00-2)
• EPA Substance Registry System: 5-CARBOXYOXINDOLE(102359-00-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-36/37
• Hazardous Substances Data: 102359-00-2(Hazardous Substances Data)

Usage

General Description

5-Carboxyoxindole is a chemical compound with the molecular formula C9H7NO3. It is a derivative of oxindole and belongs to the class of organic compounds known as indoles. 5-Carboxyoxindole plays a role in various biological processes and has potential applications in the pharmaceutical industry as a building block for the synthesis of various drug molecules. It has also been studied for its potential anti-cancer and anti-inflammatory properties. Additionally, research has shown that 5-Carboxyoxindole has the ability to inhibit the activity of certain enzymes, making it a promising candidate for the development of enzyme inhibitors for therapeutic purposes. Overall, 5-Carboxyoxindole is a versatile compound with potential uses in drug discovery and development.

InChI:InChI=1/C9H7NO3/c11-8-4-6-3-5(9(12)13)1-2-7(6)10-8/h1-3H,4H2,(H,10,11)(H,12,13)/p-1

Upstream product

• 199328-10-4 methyl 2-oxoindoline-5-carboxylate 
• 150-13-0 4-amino-benzoic acid 
• 17122-78-0 4-(2-hydroxyimino-acetylamino)-benzoic acid 
• 25128-32-9 1H-indole-2,3-dione-5-carboxylic acid 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 59-48-3 2-oxoindole 
• 65435-04-3 5-chloroacetylindolin-2-one 

Downstream Products

• 102358-72-5 5-(4-benzyl-1-piperazinylcarbonyl)oxindol 
• 1374752-85-8 5-(4-(4-acetylphenyl)piperazine-1-carbonyl)indolin-2-one 
• 1168720-81-7 2-oxo-N-phenylindoline-5-carboxamide 

Relevant articles and documents

Novel Human Aminopeptidase N Inhibitors: Discovery and Optimization of Subsite Binding Interactions

Aminopeptidase N (APN/CD13) is a zinc-dependent M1 aminopeptidase that contributes to cancer progression by promoting angiogenesis, metastasis, and tumor invasion. We have previously identified hydroxamic acid-containing analogues that are potent inhibitors of the APN homologue from the malarial parasite Plasmodium falciparum M1 aminopeptidase (PfA-M1). Herein, we describe the rationale that underpins the repurposing of PfA-M1 inhibitors as novel APN inhibitors. A series of novel hydroxamic acid analogues were developed using a structure-based design approach and evaluated their inhibition activities against APN. N-(2-(Hydroxyamino)-2-oxo-1-(3′,4′,5′-trifluoro-[1,1′-biphenyl]-4-yl)ethyl)-4-(methylsulfonamido)benzamide (6ad) proved to be an extremely potent inhibitor of APN activity in vitro, selective against other zinc-dependent enzymes such as matrix metalloproteases, and possessed limited cytotoxicity against Ad293 cells and favorable physicochemical and metabolic stability properties. The combined results indicate that compound 6ad may be a useful lead for the development of anticancer agents.

Design, synthesis, structure-activity relationships study and X-ray crystallography of 3-substituted-indolin-2-one-5-carboxamide derivatives as PAK4 inhibitors

We have previously described the identification of indolin-2-one-5-carboxamides as potent PAK4 inhibitors. This study expands the structure-activity relationships on our original series by presenting several modifications in the lead compounds, 2 and 3. A series of novel derivatives was designed, synthesized, and evaluated in biochemical and cellular assay. Most of this series displayed nanomolar biochemical activity and potent antiproliferative activity against A549 and HCT116 cells. The representative compound 10a exhibited excellent enzyme inhibition (PAK4 IC50 = 25 nM) and cellular potency (A549 IC50 = 0.58 μM, HCT116 IC50 = 0.095 μM). An X-ray structure of compound 10a bound to PAK4 was obtained. Crystallographic analysis confirmed predictions from molecular modeling and helped refine SAR results. In addition, Compound 10a displayed focused multi-targeted kinase inhibition, good calculated drug-likeness properties. Further profiling of compound 10a revealed it showed weak inhibitory activity against various isoforms of human cytochrome P450.

Discovery of indolin-2-one derivatives as potent PAK4 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study

Utilizing a pharmacophore hybridization approach, a novel series of substituted indolin-2-one derivatives were designed, synthesized and evaluated for their in vitro biological activities against p21-activated kinase 4. Compounds 11b, 12d and 12g exhibited the most potent inhibitory activity against PAK4 (IC50?=?22?nM, 16?nM and 27?nM, respectively). Among them, compound 12g showed the highest antiproliferative activity against A549 cells (IC50?=?0.83?μM). Apoptosis analysis in A549 cells suggested that compound 12g delayed cell cycle progression by arresting cells in the G2/M phase of the cell cycle, retarding cell growth. Further investigation demonstrated that compound 12g strongly inhibited migration and invasion of A549 cells. Western blot analysis indicated that compound 12g potently inhibited the PAK4/LIMK1/cofilin signalling pathways. Finally, the binding mode between compound 12g with PAK4 was proposed by molecular docking. A preliminary ADME profile of the compound 12g was also drawn on the basis of QikProp predictions.