1158560-66-7

Basic information

• Product Name: (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carbonyl chloride
• Synonyms: (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carbonyl chloride
• CAS NO: 1158560-66-7
• Molecular Formula: C₁₆H₁₂ClFN₂O₂
• Molecular Weight: 318.73
• EINECS: -0
• Mol File: 1158560-66-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carbonyl chloride(1158560-66-7)
• EPA Substance Registry System: (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carbonyl chloride(1158560-66-7)

Safety Data

• Hazardous Substances Data: 1158560-66-7(Hazardous Substances Data)

Usage

Description

(Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carbonyl chloride is a synthetic organic compound characterized by the presence of a pyrrole ring with a carbonyl chloride group and a fluorine-substituted oxindole ring with a methylidene group. (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carbonyl chloride holds potential for applications in medicinal chemistry and drug development due to its unique structural features and reactivity.

Uses

Used in Medicinal Chemistry:
(Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carbonyl chloride is used as a building block for the synthesis of complex molecules in medicinal chemistry. The presence of the carbonyl chloride group allows for reactions with nucleophiles, facilitating the creation of a diverse range of pharmaceutically relevant compounds.
Used in Drug Development:
In the pharmaceutical industry, (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carbonyl chloride is used as a key intermediate for the development of novel drugs. The fluorine atom in the oxindole ring may provide unique chemical and biological properties, making the compound a valuable candidate for further investigation and potential therapeutic applications.
Used in Organic Synthesis:
(Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carbonyl chloride serves as a versatile reagent in organic synthesis, particularly for the formation of more complex molecular structures. Its reactivity with nucleophiles and the potential for further functionalization make it a valuable component in the synthesis of various organic compounds.

Upstream product

• 253870-02-9 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid 
• 56341-41-4 5-fluoroindol-2(3H)-one 
• 356068-93-4 5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid 

Downstream Products

• 557795-19-4 sunitinib 
• 1227960-76-0 tert-butyl (Z)-(2-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)ethyl)carbamate 
• 326914-17-4 (Z)-N-(2-(dimethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide 
• 356068-97-8 N-Desethyl Sunitinib 
• 873077-70-4 (Z)-N-(2-aminoethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide 

Relevant articles and documents

Substituted oxindol-3-ylidenes as AMP-activated protein kinase (AMPK) inhibitors

AMP-activated protein kinase (AMPK) is a central metabolic regulator that promotes cancer growth and survival under hypoxia and plays a role in the maintenance of cancer stem cells. A major challenge to interrogating the potential of targeting AMPK in cancer is the lack of potent and selective small molecule inhibitors. Compound C has been widely used as an AMPK inhibitor, but it lacks potency and has a poor selectivity profile. The multi-kinase inhibitor, sunitinib, has demonstrated potent nanomolar inhibition of AMPK activity and has scope for modification. Here, we have designed and synthesized several series of oxindoles to determine the structural requirements for AMPK inhibition and to improve selectivity. We identified two potent, novel oxindole-based AMPK inhibitors that were designed to interact with the DFG motif in the ATP-binding site of AMPK, this key feature evades interaction with the common recptor tyrosine kinase targets of sunitinib. Cellular engagement of AMPK by these oxindoles was confirmed by the inhibition of phosphorylation of acetyl-CoA carboxylase (ACC), a known substrate of AMPK, in myeloid leukemia cells. Interestingly, although AMPK is highly expressed and activated in K562 cells these oxindole-based AMPK inhibitors did not impact cell viability or result in significant cytotoxicity. Our studies serve as a platform for the further development of oxindole-based AMPK inhibitors with therapeutic potential.

AMP-ACTIVATED PROTEIN KINASE INHIBITORS AND METHODS OF MAKING AND USING THE SAME

The present disclosure relates to compounds of Formula (I): (I); stereoisomers thereof, prodrugs thereof, and pharmaceutically acceptable salts thereof. The present disclosure also relates to uses of the compounds, e.g., to inhibit AMP-Activated protein kinase (AMPK) and treat cancer in a subject.

POLYMORPHS OF SUNITINIB BASE AND PROCESSES FOR PREPARATION THEREOF

The present invention provides polymorphs of Sunitinib base and processes for preparation thereof.