175075-24-8

Basic information

• Product Name: 5-Aminosulfonyl-2-Ox-Indole
• Synonyms: 5-Aminosulfonyl-2-Ox-Indole;2,3-Dihydro-2-oxo-1H-indole-5-sulfonamide;2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide;2-Oxoindoline-5-sulfonamide;5-Aminosulfonyl-2-indolinone
• CAS NO: 175075-24-8
• Molecular Formula: C₈H₈N₂O₃S
• Molecular Weight: 212.23
• Product Categories: Chemical Amines;Amines;Aromatics;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 175075-24-8.mol

Chemical Properties

• Appearance: /
• Density: 1.516g/cm³
• Refractive Index: 1.636
• Solubility: Dichloromethane, DMSO, THF
• PKA: 9.82±0.20(Predicted)
• CAS DataBase Reference: 5-Aminosulfonyl-2-Ox-Indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Aminosulfonyl-2-Ox-Indole(175075-24-8)
• EPA Substance Registry System: 5-Aminosulfonyl-2-Ox-Indole(175075-24-8)

Safety Data

• Hazardous Substances Data: 175075-24-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Aminosulfonyl-2-Ox-Indole is used as a synthetic intermediate for the development of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Aminosulfonyl-2-Ox-Indole is used as a key component in the synthesis of novel drug candidates. Its incorporation into drug molecules can potentially enhance their pharmacological properties, such as potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
5-Aminosulfonyl-2-Ox-Indole is also utilized in the agrochemical industry for the development of new pesticides and other crop protection agents. Its unique chemical structure can be exploited to create molecules with improved activity against pests and diseases, as well as enhanced safety and environmental profiles.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 5-Aminosulfonyl-2-Ox-Indole can be used as a starting material for the synthesis of various dyes and pigments. Its light-brown solid appearance suggests that it may contribute to the color properties of the final products, potentially leading to the development of new colorants with unique characteristics.
Used in Research and Development:
5-Aminosulfonyl-2-Ox-Indole is also valuable in research and development settings, where it can be used to explore new reaction pathways, study the effects of structural modifications on molecular properties, and develop new synthetic methodologies. Its use in research can contribute to the advancement of chemical science and the discovery of innovative applications across various industries.

InChI:InChI=1/C8H8N2O3S/c9-14(12,13)6-1-2-7-5(3-6)4-8(11)10-7/h1-3H,4H2,(H,10,11)(H2,9,12,13)

Upstream product

• 59-48-3 2-oxoindole 
• 199328-31-9 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 
• 175075-25-9 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid 

Downstream Products

• 622387-85-3 SyK inhibitor 
• 181223-16-5 3-(1H-indol-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide 

Relevant articles and documents

Design and synthesis of aminopropyl tetrahydroindole-based indolin-2-ones as selective and potent inhibitors of Src and Yes tyrosine kinase

A novel series of substituted 3-[3-(aminopropyl)-4,5,6,7-tetrahydro-1H- indol-2-ylmethylene]-1,3-dihydro-indole-2-ones was discovered as potent inhibitors of the non-receptor tyrosine kinase Src and Yes. A structure-activity relationship was developed in order to optimize their potency and selectivity. Syntheses of these compounds are also described herein.

Hexahydro-cyclohepta-pyrrole oxindole as potent kinase inhibitors

The present invention is directed to a class indolinone compounds, hexahydro-cyclohepta-pyrrole oxindoles, which are useful as protein kinase inhibitors.

5-sulfonamido-substituted indolinone compounds as protein kinase inhibitors

The present invention relates to 5-sulfonamido substituted indolinones that modulate the activity of protein kinases (“PKs”). The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.

Sulfonamide substituted indolinones as inhibitors of DNA dependent protein kinase (DNA-PK)

The present invention relates generally to the field of radiosensitizing agents which are capable of enhancing radiotherapy by inhibiting DNA-PK (DNA-protein kinase). In particular, it relates to sulfonamide substituted indolinones which inhibit DNA-PK.

Potent small molecule inhibitors of spleen tyrosine kinase (Syk)

A series of oxindoles demonstrating inhibition of the phosphorylation of biotinylated substrates of Syk and IgE/FcεRI triggered basophil cell degranulation has been identified. A study of the SAR around sulfonamide 31 (IC50=5 nM, EC50=1400 nM) is discussed. The modest cellular activity representative of the sulfonamide series was overcome when the Polar Surface Area was lowered to 2, leading to the identification of amide 32 (IC50=145 nM, EC50=100 nM).

Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives

The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

Combination therapy for the treatment of cancer

The present invention relates to methods for treatment or prevention of neoplasia disorders using protein tyrosine kinase inhibitors in combination with cyclooxygenase inhibitors, in particular cyclooxygenase-2 selective inhibitors.

Indolinone derivatives as protein kinase/phosphatase inhibitors

The present invention relates to certain 2-indolinone compounds which modulate the activity of protein kinases (“PKs”) and phosphatases. The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.