150544-01-7

Basic information

• Product Name: 6-amino-5-fluoroindolin-2-one
• Synonyms: 6-amino-5-fluoroindolin-2-one;6-amino-5-fluoro-1,3-dihydro-2H-Indol-2-one
• CAS NO: 150544-01-7
• Molecular Formula: C₈H₇FN₂O
• Molecular Weight: 166.1523832
• EINECS: -0
• Mol File: 150544-01-7.mol

Chemical Properties

• Boiling Point: 383.528 °C at 760 mmHg
• Flash Point: 185.751 °C
• Appearance: /
• Density: 1.414 g/cm³
• CAS DataBase Reference: 6-amino-5-fluoroindolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-5-fluoroindolin-2-one(150544-01-7)
• EPA Substance Registry System: 6-amino-5-fluoroindolin-2-one(150544-01-7)

Safety Data

• Hazardous Substances Data: 150544-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
6-amino-5-fluoroindolin-2-one is utilized as a key intermediate in the synthesis of fluorinated indole derivatives. These derivatives are valued for their biological activity, making them essential components in the development of new pharmaceuticals. 6-amino-5-fluoroindolin-2-one serves as a building block for creating molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, 6-amino-5-fluoroindolin-2-one is used as a versatile reagent for the preparation of various complex organic molecules. Its unique structure allows for multiple synthetic pathways, facilitating the creation of a wide range of chemical entities with diverse properties and potential uses.
Used in Research Applications:
6-amino-5-fluoroindolin-2-one is employed as a research tool in academic and industrial laboratories. It is used to study the effects of fluorination on the properties of indole derivatives, which can lead to insights into their reactivity, stability, and potential interactions with biological targets. This research can contribute to the advancement of drug discovery and the understanding of molecular mechanisms.

Upstream product

• 1082989-85-2 (2,4-diamino-5-fluoro-phenyl)-acetic acid 
• 331-25-9 (3-fluorophenyl)acetic acid 
• 150544-00-6 methyl (5-fluoro-2,4-dinitrophenyl)acetate 
• 1025909-27-6 (2,4-Diamino-5-fluoro-phenyl)-acetic acid methyl ester 

Downstream Products

• 945381-82-8 5-fluoro-6-(4-fluoro-benzylamino)-1,3-dihydro-indol-2-one 
• 1621584-46-0 N-(5-fluoro-2-oxoindolin-6-ylcarbamoyl)-2-fluoro-4-methoxybenzamide 
• 1621584-45-9 N-(5-fluoro-2-oxoindolin-6-ylcarbamoyl)-4-methoxybenzamide 
• 945379-44-2 N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxy-acetamide 

Relevant articles and documents

Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia

A series of 6-acylureido derivatives containing a 3-(pyrrol-2- ylmethylidene)indolin-2-one scaffold were synthesized as potential dual Aurora B/FLT3 inhibitors by replacing the 6-arylureido moiety in 6-arylureidoindolin-2- one-based multi-kinase inhibitors. (Z)-N-(2-(pyrrolidin-1-yl)ethyl)-5-((6-(3-(2- fluoro-4-methoxybenzoyl)ureido)-2-oxoindolin-3-ylidene)methyl)-2, 4-dimethyl-1H-pyrrole-3-carboxamide (54) was identified as a dual Aurora B/FLT3 inhibitor (IC50 = 0.4 nM and 0.5 nM, respectively). Compound 54 also exhibited potent cytotoxicity with single-digit nanomolar IC50 values against the FLT3 mutant-associated human acute myeloid leukemia (AML) cell lines MV4-11 (FLT3-ITD) and MOLM-13 (FLT3-ITD). Compound 54 also specifically induced extrinsic apoptosis by inhibiting the phosphorylation of the Aurora B and FLT3 pathways in MOLM-13 cells. Compound 54 had a moderate pharmacokinetic profile. The mesylate salt of 54 efficiently inhibited tumor growth and reduced the mortality of BALB/c nude mice (subcutaneous xenograft model) that had been implanted with AML MOLM-13 cells. Compound 54 is more potent than sunitinib not only against FLT3-WT AML cells but also active against sunitinib-resistant FLT3-ITD AML cells. This study demonstrates the significance of dual Aurora B/FLT3 inhibitors for the development of potential agents to treat AML.

INDOLIN-2-ONE DERIVATIVES AS PROTEIN KINASE INHIBITORS

A novel class of indoline-2-one derivatives are disclosed. These compounds are protein kinase inhibitors which are useful for treating hyperproliferative diseases such as cancer.

PYRROLO-NITROGENOUS HETEROCYCLIC DERIVATIVES, THE PREPARATION AND THE PHARMACEUTICAL USE THEREOF

The invention provides new pyrrolo-nitrogenous heterocyclic derivatives represented by formula (I) or their salts, the preparation thereof, pharmaceutical compositions containing such derivatives and the use of such derivatives as therapeutic agents, espe

2-(2-OXOINDOLINE-3-YLIDENE)METHYL-5-(2-HYDROXY-3-MORPHOLIN-4-YL -PROPYL)-6,7-DIHYDRO -1H- PYRROL[3,2-C]PYRIDINE-4(5H)-ONE COMPOUNDS AND USE AS PROTEIN KINASE INHIBITORS

Pyrrolo[3,2-c]pyridine-4-one-2-indolinone compounds, especially 2-(2-oxoindoline-3-ylidene)methyl-5-(2-hydroxy-3-morpholin-4-yl-propyl)-6,7-dihyd ro-1H-pyrrol[3,2-c]pyridine-4(5H)-one compounds. Their preparation and pharmaceutical composition, and pharma

2-(2-OXOINDOLINE-3-YLIDENE)METHYL-5-(2-HYDROXY-3-MORPHOLIN-4-YL-PROPYL)-6,7-DIHYDRO-1H-PYRROL[3,2-C]PYRIDINE-4(5H)-ONE COMPOUNDS AND USE AS PROTEIN KINASE INHIBITORS

Pyrrolo[3,2-c]pyridine-4-one-2-indolinone compounds, especially 2-(2-oxoindoline-3-ylidene)methyl-5-(2-hydroxy-3-morpholin-4-yl-propyl)-6,7-dihydro-1H-pyrrol[3,2-c]pyridine-4(5H)-one compounds. Their preparation and pharmaceutical composition, and pharmac

IMIDAZOLE DERIVATIVES AS FUNCTIONALLY SELECTIVE ALPHA2C ADRENORECEPTOR AGONISTS

In its many embodiments, the present invention provides imidazole derivatives which are inhibitors of alPha2C adrenergic receptor agonists, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition or amelioration of one or more conditions associated with the alpha2C adrenergic receptors using such compounds or pharmaceutical compositions. Formula (I).

Preparation and alkylation of regioisomeric tetrahydrophthalimide-substituted indolin-2(3H)-ones

A series of novel regioisomeric tetrahydrophthalimide-substituted indolin-2-ones has been prepared via the Sommelet-Hauser type cyclization of appropriately substituted anilines as potential herbicides. The resultant indolin-2-ones were then regioselectively alkylated at N-1 and C-3 to give 1,3,3-trisubstituted indolin-2-ones. The most active series was also prepared by the bis-nitration of m-fluorophenylacetic acid followed by reduction and cyclization to give 6-amino-5-fluoroindolin-2-one. Elaboration to the tetrahydrophthalimide-substituted indolin-2-one was followed by C- and N-alkylation to give the desired compounds.

Substituted indolinones useful as herbicidal agents

Substituted indolinone compounds which are effective in the control of undesirable plant species are described. Also described are a method for the herbicidal use of the compounds and a method for their preparation.